6 ms·

Hi, I had a startup fail after we (I had 1 co-founder) invested ~4 years into it. Some thoughts: A startup failing is not a rational thing. At this time emotio

by Maro 8y ago

Hi, I had a startup fail after we (I had 1 co-founder) invested ~4 years into it. Some thoughts: A startup failing is not a rational thing. At this time emotions (regret, fear, stress, depression) take over, it's a tough time to handle. If it's tough for you, take comfort in knowing that it's tough for everyone. When I was going through this, I couldn't handle the stress, so it spilled over into my personal life, and in the end I also got divorced a few months after the startup failed. Avoid that by not prolonging the process. Talking to too many people isn't that helpful. Most "naive" people (who haven't done this, who don't understand how tech companies work, etc) will just tell you to push on. They will do so simply because it's baked into our Culture, that when somebody is in trouble you should be positive to them, tell them not to quit, the way you would fire up a runner at a Marathon race. But a startup is NOT a Marathon race, because training for and finishing a Marathon is purely up to you, but that's simply not true for a startup. (As a Marathon runner, this was one of my misconceptions going into my startup.) Here on HN we're okay with failure, but outside this bubble it's not that okay. So if you talk to people (friends, relatives) you'll get roughly the same if you told them about "I'm dating a girl and it's not working out that great" or "I have a new job but it's not working out that great", most advice would be pretty useless and just along the lines of Try Harder. So you have to learn to ignore these non-expert opinions. The fact that they may be investors sucks. It sounds like you really don't believe it's going to work out. Don't spend another 3-6 months proving to whoever's left (clients/investors) that it doesn't work, just so they "let you" off the hook. As somebody else said, go on a vacation, and if you still want to stop it, stop it. One final thing: when I was going through this, I was constantly projecting bad outcomes, which in this first world scenario is a few tough/uncomfortable conversations/situations with people. In the end, some of these happened, but overall it was maybe 1-2 hours worth of conversations, which really weren't that tough/uncomfortable in the end. In retrospect, the fact that I stressed over it 24/7 for months (so, 100s of hours) was really stupid and irrational, so don't do that. One final trick: imagine yourself 3 years down the line. EVERYTHING WILL BE ALL RIGHT. Good luck :)

eight_ender 8y ago
As someone who worked as a CTO at what I like to call a "zombie" startup I agree with the poster above me, and it hurts just to recollect the history. You can keep this shit up indefinitely. We're in a weird environment where, with enough endurance, a startup, even one with a miserable high touch sales cycle and poor business model, can live month to month like some sort of crime family looking for the next big score. If you go this route you'll score a contract or two, and you'll think you're growing. You'll hire on a brilliant employee and then fire them a few months later when the money dries up. Your heart will break. Your workload will increase. You'll start leaning on contractors because FTEs need consistent revenue, and your shit investors insist on offshore labour because they don't know any better. Contractors suck and their code sucks unless supervised, so you'll decide to do it yourself. Your investors will get unhappy and your partner will find another naive low tier investor to buy them out and start the cycle over. Your share in the company will drop each time you do this. Your counterpart will spend 1/3rd of their time appeasing the investors and the other 2/3rds attempting to be a top shelf B2B sales exec / account manager which they are not. They will get absolutely abused in the sales cycle and concede to shit they shouldn't. You will continue to burn the candle at both ends like a good technical leader in a crisis and then burn out, believing the entire time that technical superiority alone will win the day. I'm painting a really bleak picture here, but only because I got out after three years of this when I finally realized the nature of the endless cycle of a cockroach startup. The company I worked for is still going, against all odds. Fuck maybe they go forever. I know people who still work there, and from all accounts it's an endless groundhog day of zero growth and pain. Don't be that startup, if the business model is in peril this early on don't extend the pain, just pull the ripcord and, above all else, try to learn from the experience.
- mac330 8y ago
  > Contractors suck and their code sucks unless supervised I have worked both as an contractor and as FTE for product/service companies (and startups), and I'm a bit tired with fighting with this prejudice. The core business of software houses is ... making software, and making it such way that a client is happy with the outcome, pays for what he really need and returns with more projects. Startups / product companies focus on various business domains and software is a byproduct of their operation. Byproduct that is often driven by chaotic business decisions. Good software houses enforce specification on clients (real specification, not wishes) to make sure they know what they want or need. Good software houses implement and follow correct software development process that enables success of a project (not pseudo Scrum with slapped Kanban sticker on it). I could can add the many FTEs are stuck for years with deprecated technologies, they don't have practical overview and hand-on experience with new technologies and paid, off the shelf solution. Large part of startups literally burned resources on reinventing wheels, because FTEs where convinced that they can do something better than using a ready solution, or they had no idea that such solution existed. Software houses are familiar with dozens of technologies because they create and maintain dozens of different, large and small projects from various domains.
  - dabockster 8y ago
    I think he/she was talking more about hiring cheap freelancers for temp work or engaging in some sort of contractor misclassification due to investor pressure.
  - Daft_but_happy 8y ago
    Most startups fall into one of two categories, either they have the financial side covered or they have the technical side covered, they hardly ever have both. The financial people need contractors, but they have no clue how to find a decent, honest one, and even if they luck out and find one, they don't know how to work with one. Either way, contractors get a bad rep. I've seen some horrible ones who honestly deserve a bad reputation and more, but I've also seen some really good ones get a bad reputation due to impossible deadlines, poor or no specification or thrashing due to changing the specification of what should be delivered several times a week.
ireadfaces 8y ago
I second what you said here. I worked as a CTO of a start up which was primarily driven by ego and lies of the CEO. He didn't want to go a rational way and constantly duped (yes duped) investors. I took a long time to exit the startup. Reason? Because I was not able to think through it, because when you are so much into something you can't think without it affecting your thoughts. But slowly and steadily I was able to judge the situation by thinking practically (keep thinking, many be write your points, that helps). So for me, best thing was to get out we that company was not going anywhere, may be not the same for you. After four months I joined a very successful bootstrapped startup in tech role. It is an individual contributor role. But I am learning, and preparing for my next feat. Life goes on.

by Maro 8y ago

eight_ender 8y ago

As someone who worked as a CTO at what I like to call a "zombie" startup I agree with the poster above me, and it hurts just to recollect the history. You can keep this shit up indefinitely. We're in a weird environment where, with enough endurance, a startup, even one with a miserable high touch sales cycle and poor business model, can live month to month like some sort of crime family looking for the next big score. If you go this route you'll score a contract or two, and you'll think you're growing. You'll hire on a brilliant employee and then fire them a few months later when the money dries up. Your heart will break. Your workload will increase. You'll start leaning on contractors because FTEs need consistent revenue, and your shit investors insist on offshore labour because they don't know any better. Contractors suck and their code sucks unless supervised, so you'll decide to do it yourself. Your investors will get unhappy and your partner will find another naive low tier investor to buy them out and start the cycle over. Your share in the company will drop each time you do this. Your counterpart will spend 1/3rd of their time appeasing the investors and the other 2/3rds attempting to be a top shelf B2B sales exec / account manager which they are not. They will get absolutely abused in the sales cycle and concede to shit they shouldn't. You will continue to burn the candle at both ends like a good technical leader in a crisis and then burn out, believing the entire time that technical superiority alone will win the day. I'm painting a really bleak picture here, but only because I got out after three years of this when I finally realized the nature of the endless cycle of a cockroach startup. The company I worked for is still going, against all odds. Fuck maybe they go forever. I know people who still work there, and from all accounts it's an endless groundhog day of zero growth and pain. Don't be that startup, if the business model is in peril this early on don't extend the pain, just pull the ripcord and, above all else, try to learn from the experience.

mac330 8y ago
> Contractors suck and their code sucks unless supervised I have worked both as an contractor and as FTE for product/service companies (and startups), and I'm a bit tired with fighting with this prejudice. The core business of software houses is ... making software, and making it such way that a client is happy with the outcome, pays for what he really need and returns with more projects. Startups / product companies focus on various business domains and software is a byproduct of their operation. Byproduct that is often driven by chaotic business decisions. Good software houses enforce specification on clients (real specification, not wishes) to make sure they know what they want or need. Good software houses implement and follow correct software development process that enables success of a project (not pseudo Scrum with slapped Kanban sticker on it). I could can add the many FTEs are stuck for years with deprecated technologies, they don't have practical overview and hand-on experience with new technologies and paid, off the shelf solution. Large part of startups literally burned resources on reinventing wheels, because FTEs where convinced that they can do something better than using a ready solution, or they had no idea that such solution existed. Software houses are familiar with dozens of technologies because they create and maintain dozens of different, large and small projects from various domains.
- dabockster 8y ago
  I think he/she was talking more about hiring cheap freelancers for temp work or engaging in some sort of contractor misclassification due to investor pressure.
- Daft_but_happy 8y ago
  Most startups fall into one of two categories, either they have the financial side covered or they have the technical side covered, they hardly ever have both. The financial people need contractors, but they have no clue how to find a decent, honest one, and even if they luck out and find one, they don't know how to work with one. Either way, contractors get a bad rep. I've seen some horrible ones who honestly deserve a bad reputation and more, but I've also seen some really good ones get a bad reputation due to impossible deadlines, poor or no specification or thrashing due to changing the specification of what should be delivered several times a week.

ireadfaces 8y ago

I second what you said here. I worked as a CTO of a start up which was primarily driven by ego and lies of the CEO. He didn't want to go a rational way and constantly duped (yes duped) investors. I took a long time to exit the startup. Reason? Because I was not able to think through it, because when you are so much into something you can't think without it affecting your thoughts. But slowly and steadily I was able to judge the situation by thinking practically (keep thinking, many be write your points, that helps). So for me, best thing was to get out we that company was not going anywhere, may be not the same for you. After four months I joined a very successful bootstrapped startup in tech role. It is an individual contributor role. But I am learning, and preparing for my next feat. Life goes on.