There’s one night that stands out as the hardest night in all my time as an entrepreneur–without comparison (Not even the night I put my fist through a glass door can compete). It’s quite naturally the night we realise that we probably won’t make it, under the worst imaginable circumstances. First, a little backstory The higher you fly, the deeper you fall. Our hubris had been roughly three months earlier, when we went on the Danish version of Shark Tank/Dragons Den, pitching our company and asking for DKK 300k (≈$46k). We had done our homework, and delivered a pitch that was, in my humble opinion, fucking awesome. We sold our vision, and we had the answers. Several of the high profile investors were interested, and we ended up walking out of there with a interest of a million Kroner (≈$150k. — More than three times of what we asked for. This was the most amazing day. As anyone who’s walked away from a really, really great investor meeting will know, you feel like you’re flying. On top of this, we were going to get some serious PR from this, as the show was extremely popular. Of course, when you get a commitment while recording a TV-show, that’s only a commitment to start a due diligence, and we were in for a rough one. As first time founders, dealing with some of the world’s best investors isn’t easy. They were fair, honest, and to the point, but there were clear problems in our startup that made them weary of putting down the full investment. On a call with the investors, one of them said it very, beautifully: Your team is awesome, your product sucks It was true. And we had to fix it. We had already tried to bring in more manpower, but being non-technical, we struggled to find the right guys for the job. In the end, we set a goal with our investors: By the time the show aired, we needed to have our product improved on range of areas, otherwise they would pull their investment. We didn’t. Showtime On the day of the show, we were still working like crazy, and pushing our developers well beyond what was probably fair, but everyone knew the cold hard truth: The show will air at 21.00, and if we aren’t done by that time, we are probably done all together. We ran out of time before the show, and this let to what will by far be the single most depressing moment of my professional life. Sitting in an empty office with my cofounders, all of us watching 100s of messages popping in saying “congratulations”, “I knew you could do it”, “You are killing it!” and “I knew you could do it”. In short: The exact opposite feelings of what we had at the moment. Full attention, full failure. Hard things. Southbound & down Around midnight there’s basically nothing more to do, and I walk out in the night to take the U-bahn down to my flat in Kreuzberg. Mood darker than the tunnel around the U8, time couldn’t pass fast enough until I could be alone on my Graefestraße balcony; drinking Netto’s €2 bio-wine and speed-rolling cigarettes like I was getting paid for it. — A job I could actually have considered at this point. Naturally, this is when the conductor announces that the train won’t go any further, and that everyone has to get off. Because fuck me. In the five or ten minutes up to this, an annoyingly cheerful stranger had continuously been trying to strike up conversation with me. I’d tried my best at ignoring him, but his continuous smiling and questions made it increasingly hard. As he spoke no German and very poor English, I decide to help him get from one train to the next. He had already asked for directions several times, despite him being on the right train and just needing to stay seated. Anyway, we start talking, and his ridiculously optimistic attitude started to rub off. Pretty soon, we were both laughing, and I start asking him about his background. Turns out, he’d walked to Berlin, all the way from fucking Syria, and was working every single night from 01 am to noon in order to make a living. I was feeling super depressed because the most likely outcome of a dream I’d chosen to follow was starting to kick in. This guy’s name is Prince, and he’s reminding me that I shouldn’t focus on the shit that was behind me, but on the upside of where I am right now. This isn’t a, “I should feel so grateful for what I have, there are poor kids in Africa”-kinda post. It’s a enjoy the fucking ride, sometimes it’s low, but make sure the lows are in good places with good people. Soft things. Prince was crazy excited about just being in Berlin, and so was I. I just needed a reminder. The show mustn’t go on I think in any failed startup, there’s two breaking points: 1) The one where your company actually fails, and 2) the one where you come to the realisation that it has failed. Our company probably failed a lot sooner than we realised. It’s the classic story of not having a tech guy on the team from the beginning, and even though we worked day and night to make things work, we just didn’t have what it took. I’ve learned an incredible amount of things, and when (not if), I take on my next venture, there are a lot fewer things I’ll do wrong, but still there are more mistakes yet to be made than I’ve made in the past. The most important thing however, is not which mistakes you make or don’t make, it who you make them with. I had the incredible luck to start my companies people I’d only just met: My amazing co-founders, living our dream in Berlin (And looking like total idiots, of course) I think the most amazing thing about this whole journey is, that I didn’t know these guys when we started, but now I have friends for life. In all the shit we went through, we never had an actual fight. Sure we had lots of heated discussions, but they were never about personality, only the company. To this day, this is what makes me look back at this with a smile on my face. East & up I live in Tallinn Estonia now, where I’ve landed a job in an amazing company, in a role I probably never would’ve landed if it weren’t for all the stuff we went through with Trunkbird. I recently met with one of my cofounders in Berlin, and had an amazing talk, making me sure we’ll do much more together in the future, and the other is actually joining me in Tallinn! Thanks to you two, and to all the other amazing people who helped me get through all this. Remember the soft things, it’s what get you through the hard.