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This is eerily similar to a job I had. I also worked for a young asshole CEO called Andrew, with multiple rubbish businesses, pretending to have more money than

This is eerily similar to a job I had. I also worked for a young asshole CEO called Andrew, with multiple rubbish businesses, pretending to have more money than he had, having no idea what he was doing, and faced jail time a few years after I left. If you replace "property market" with "education sector" and "UK" with "Australia" we could have almost written the exact same article. I wonder how many of these companies are out there. Be wary of CEOs that don't bring anything other than money to the table. The more useless someone is, the more of a cunt they can be. Obviously this guy was struggling to pay his rent so he was going to take whatever job came up, but if you're entering startups and have the privilege of a bit of money in the bank and time on your side, try and pick the one with founders that are actually doing the work themselves. Look for some proof that they've built, designed or sold something substantial, before you agree to do all the work for them. Because if they haven't even begun to do the hard yards themselves, they're not likely to respect any of your work.

gjvc 5y ago
I wish I had read this several years ago. This is the kind of thing which everyone instinctively knows but somehow forgets with age, or ignores due to circumstances (like needing a job having just been made redundant). I swear that CEOs like the one mentioned here specifically prefer hiring those who are in need like this, with the predictable awful behaviours. Some people will get lucky, but I expect that they are the exceptions, not the rule. Avoid startups where the CEO does / has done nothing but sales. Avoid them like the absolute plague that they are. If you are in such a place already, and you think things will get better, then I have a bridge to sell you. It is vanishingly likely that they won't, if only for the simple fact that the CEO has found a formula which works, and has no motivation to change it, and your best bet is to leave ASAP for the wider world which has infinitely more opportunity. (BTW, you won't succeed in changing such a "culture" for the better, so don't even think about it. I know you have.) I could ramble on for several paragraphs, but BigJono has summed it up pretty concisely so I will proffer just this advice when sizing up CEOs and opportunities: Remember, if there is any doubt, then there is no doubt.
- fsloth 5y ago
  As a counter example - I was at a startup where all the CEO did was sales. Everything worked really great. I think the key here is is the culture pathological or not - not the specific role of the CEO. CEO can have good enough understanding of tech to do their job well even thought they are not elbows deep in it themselves.
  - jjoonathan 5y ago
    Culture is important, but I think direction might be even more key. If "sales" means "I spent 3 years talking to every customer in a particular industry, became keenly aware of a vacant niche, and now am looking to do something about it" I reckon it would be a very good thing. If "sales" means "I saw that the crypto market is booming and want to get in on the easy money," it's not going to go well.
    - fsloth 5y ago
      Yes, very descriptive - the 'good sales CEO' was very much per your positive example.
- deleted 5y ago
  [deleted]
- rpeden 5y ago
  Perhaps give them some flexibility if there's a technical co-founder as CTO. It depends on what the startup is working on. If it's trying to sell into the enterprise I'd be a lot more confident in its future if the CEO is heavily sales-focused provided there's also a technical co-founder keeping things sane on the tech side.
  - Aeolun 5y ago
    If there is a co-founder at all that’s much better than just a single person.
    - 5y ago
ehnto 5y ago
I got a few stories from Australia I'd rather not tell online, but suffice to say there are at least a few more out there. From unpaid super, to quitting their own business, and that one guy who posted us a frozen chicken meal interstate through the regular post during an Australian summer, so we could try it out. We did not try it.
technofiend 5y ago
What is it with dodgy entrepreneurs and criminality? One of my first jobs was for a guy who after a week of mundane tasks revealed he really hired me to go through the source code of some program and change everything so it looked like he wrote it because he planned to resell it as his own. I politely declined. Turns out literally everyone there except me was an ex-con. I found a job with a different company across the hall and never looked back.
darkr 5y ago
> Look for some proof that they've built, designed or sold something substantial, before you agree to do all the work for them I disagree. 4 months working for a semi-criminal part mad-man is an amazing opportunity to learn about life and humanity. Every time I meet someone who went from straight A’s at school, to university/college and then straight into a graduate scheme at some multinational, then onwards and upwards into some successful, but otherwise shallow career I feel so sad for that person that they missed out on the beautiful weirdness of life.
- BigJono 5y ago
  That's like saying an abusive relationship is a great way to learn about life and humanity. You can get a ton of valuable experience working for a startup without a CEO that's an absolute knob. You don't have to jump straight from worst company ever to boring enterprise grad position where you don't learn anything.
  - gjvc 5y ago
    +100
lategloriousgnu 5y ago
Interesting that you mention the "education sector". That sector seems to have a huge number of dodgy "training companies" covering all sorts of industries. My first ever job, straight out of college in the UK, at 18 years old, was a Web Developer at an apprenticeship training business in Essex. The structure of the business was that it was a "training provider" for web development, design and a few other things. Rather than go to college or university, kids (usually around 16 years old) would go to this company to get "on the job" training. The company was accredited by a university, such that on completion of the "course", students would receive some sort of BTEC certificate, which is similar to a TAFE course in Australia. A requirement of "training providers" is that they provide the tutoring to the students in order to obtain the BTEC, but must also place the students into businesses for around 50% of the course time to receive their "on the job" experience. The student must have received a certain number of hours of experience at a real web development company to obtain the proper certificate from the uni. This training provider took on about 200 students a year into their web development course. Now it's impossible to place that many students with real web development companies. But for each bum on a seat, the company received a sizable chunk of cash from the government apprenticeship scheme, so it was important to get as many through the door as possible. To solve the issue, the director of the training company (a guy called John who very much matches the description of other middle-aged "pretending to be rich" guys), spun up a series of fake companies for each course, such that he would place the students in his own companies to get their "on the job" hours. Each of the companies had it's own office, but usually attached to the same main building, and some in some random industrial estates without signage. The web development company was the one I was hired in. The salary was £12,000 a year, which was just about enough for me to fill my car up and drive there from my parents house every day. Our "clients" at the web development company were all other businesses owned by John. Each of those businesses didn't seem to have any clients of their own, the whole web of businesses was driven purely from the training grants being generated by the main training company. I worked there for a year and it was a very strange experience. Half of the time I was tasked with coding up websites for the web of businesses and doing odd jobs for John's friends (I remember spending a month building a website for a youth football team). The other half of my time was spent "tutoring" the apprentices who were in my office for 50% of their course. That mostly involved giving them "briefs" for clients which didn't exist, getting them all to code up their own version and add it to their portfolio. I didn't have a boss at the web development company. On paper, I was the only full-time employee. About a year after I left in 2012, I saw on the news that the training company had folded, because the university had caught on to what was happening, and stopped their funding. The entire network of businesses now seems to have been wiped from existence.

gjvc 5y ago

I wish I had read this several years ago. This is the kind of thing which everyone instinctively knows but somehow forgets with age, or ignores due to circumstances (like needing a job having just been made redundant). I swear that CEOs like the one mentioned here specifically prefer hiring those who are in need like this, with the predictable awful behaviours. Some people will get lucky, but I expect that they are the exceptions, not the rule. Avoid startups where the CEO does / has done nothing but sales. Avoid them like the absolute plague that they are. If you are in such a place already, and you think things will get better, then I have a bridge to sell you. It is vanishingly likely that they won't, if only for the simple fact that the CEO has found a formula which works, and has no motivation to change it, and your best bet is to leave ASAP for the wider world which has infinitely more opportunity. (BTW, you won't succeed in changing such a "culture" for the better, so don't even think about it. I know you have.) I could ramble on for several paragraphs, but BigJono has summed it up pretty concisely so I will proffer just this advice when sizing up CEOs and opportunities: Remember, if there is any doubt, then there is no doubt.

fsloth 5y ago
As a counter example - I was at a startup where all the CEO did was sales. Everything worked really great. I think the key here is is the culture pathological or not - not the specific role of the CEO. CEO can have good enough understanding of tech to do their job well even thought they are not elbows deep in it themselves.
- jjoonathan 5y ago
  Culture is important, but I think direction might be even more key. If "sales" means "I spent 3 years talking to every customer in a particular industry, became keenly aware of a vacant niche, and now am looking to do something about it" I reckon it would be a very good thing. If "sales" means "I saw that the crypto market is booming and want to get in on the easy money," it's not going to go well.
  - fsloth 5y ago
    Yes, very descriptive - the 'good sales CEO' was very much per your positive example.
deleted 5y ago
[deleted]
rpeden 5y ago
Perhaps give them some flexibility if there's a technical co-founder as CTO. It depends on what the startup is working on. If it's trying to sell into the enterprise I'd be a lot more confident in its future if the CEO is heavily sales-focused provided there's also a technical co-founder keeping things sane on the tech side.
- Aeolun 5y ago
  If there is a co-founder at all that’s much better than just a single person.
  - 5y ago

ehnto 5y ago

I got a few stories from Australia I'd rather not tell online, but suffice to say there are at least a few more out there. From unpaid super, to quitting their own business, and that one guy who posted us a frozen chicken meal interstate through the regular post during an Australian summer, so we could try it out. We did not try it.

technofiend 5y ago

What is it with dodgy entrepreneurs and criminality? One of my first jobs was for a guy who after a week of mundane tasks revealed he really hired me to go through the source code of some program and change everything so it looked like he wrote it because he planned to resell it as his own. I politely declined. Turns out literally everyone there except me was an ex-con. I found a job with a different company across the hall and never looked back.

darkr 5y ago

> Look for some proof that they've built, designed or sold something substantial, before you agree to do all the work for them I disagree. 4 months working for a semi-criminal part mad-man is an amazing opportunity to learn about life and humanity. Every time I meet someone who went from straight A’s at school, to university/college and then straight into a graduate scheme at some multinational, then onwards and upwards into some successful, but otherwise shallow career I feel so sad for that person that they missed out on the beautiful weirdness of life.

BigJono 5y ago
That's like saying an abusive relationship is a great way to learn about life and humanity. You can get a ton of valuable experience working for a startup without a CEO that's an absolute knob. You don't have to jump straight from worst company ever to boring enterprise grad position where you don't learn anything.
- gjvc 5y ago
  +100

lategloriousgnu 5y ago

Interesting that you mention the "education sector". That sector seems to have a huge number of dodgy "training companies" covering all sorts of industries. My first ever job, straight out of college in the UK, at 18 years old, was a Web Developer at an apprenticeship training business in Essex. The structure of the business was that it was a "training provider" for web development, design and a few other things. Rather than go to college or university, kids (usually around 16 years old) would go to this company to get "on the job" training. The company was accredited by a university, such that on completion of the "course", students would receive some sort of BTEC certificate, which is similar to a TAFE course in Australia. A requirement of "training providers" is that they provide the tutoring to the students in order to obtain the BTEC, but must also place the students into businesses for around 50% of the course time to receive their "on the job" experience. The student must have received a certain number of hours of experience at a real web development company to obtain the proper certificate from the uni. This training provider took on about 200 students a year into their web development course. Now it's impossible to place that many students with real web development companies. But for each bum on a seat, the company received a sizable chunk of cash from the government apprenticeship scheme, so it was important to get as many through the door as possible. To solve the issue, the director of the training company (a guy called John who very much matches the description of other middle-aged "pretending to be rich" guys), spun up a series of fake companies for each course, such that he would place the students in his own companies to get their "on the job" hours. Each of the companies had it's own office, but usually attached to the same main building, and some in some random industrial estates without signage. The web development company was the one I was hired in. The salary was £12,000 a year, which was just about enough for me to fill my car up and drive there from my parents house every day. Our "clients" at the web development company were all other businesses owned by John. Each of those businesses didn't seem to have any clients of their own, the whole web of businesses was driven purely from the training grants being generated by the main training company. I worked there for a year and it was a very strange experience. Half of the time I was tasked with coding up websites for the web of businesses and doing odd jobs for John's friends (I remember spending a month building a website for a youth football team). The other half of my time was spent "tutoring" the apprentices who were in my office for 50% of their course. That mostly involved giving them "briefs" for clients which didn't exist, getting them all to code up their own version and add it to their portfolio. I didn't have a boss at the web development company. On paper, I was the only full-time employee. About a year after I left in 2012, I saw on the news that the training company had folded, because the university had caught on to what was happening, and stopped their funding. The entire network of businesses now seems to have been wiped from existence.