I think startups can be romanticized so I'm sharing my startup story and some of the things I did do and some of the things I should have done.

When I was 23 I joined a startup as employee number 4. We did Salesforce implementations for small businesses using freelancers. At the time it was the CEO, Director of Sales, and another Project manager. I was originally hired as an admin assistant but after I taught the other project manager what a Gantt chart was, the company decided I was ready for the big time.

The company eventually fell apart due to internal conflict. The CEO had already started another successful web design company during his teens. He was extremely driven, charismatic, and caring, (and better than me in almost all the ways that count) but he did seem to have lost something due to working so hard for so long. The director of Sales was an absolute beast at what he did well, which was sales. Our pipeline was always bursting, but the customers expectations were often for things that were technically impossible (integrating Salesforce with Outlook at the time was terrible). He was clinging on to a fading dream of entrepreneurship. He didn't talk about his past, but he had worked in enterprise, and started his own business, but he hadn't reached the parabolic heights that he'd hoped for. The PM (project manager) was a friend of mine, and a friend of the CEO. He was extremely smart, but sometimes an idealist, and at the time not a very experienced negotiator.

I started at the company because I had been working at a big business that didn't offer me full-time work. Straight out of university I needed a job, so I'd have quick cash. I had an Arts degree and just wanted anything to start, so I took what I could get. They had me on as a temp, and I was fearful. I wanted security and one of the ways I saw to get it was to threaten to leave, so I put out my feelers, and the PM answered. My boss at the time couldn't put me on, and even if he'd said he would, I probably would have left for the startup. I figured, it could be the next Facebook.

At the interview, the Sales guy grilled me, but one of my strong points is interviews, so I nailed it. I even asked for more money, and I got it! At the time, I didn't ask a question which I should have:

1) Ask the founders why they need another employee

Hell, this probably wouldn't have changed my answer to their offer, but at the time they were looking for relief. The PM was overworked, and they needed him supported. In retrospect, they didn't know what they wanted. I kind of wanted an assistant role, and at the time didn't know I wasn't the best at project management, but that's what I ended up doing. I think in most startups the original employees don't have much choice - they do what needs doing. Find out what that is so you know what to expect.

I also did one thing well:

2) Have a realistic discussion about money

I asked for more money than they had offered in my interview. You should already know what the startup does, and you should have a fair idea of how cash poor or rich they are. This became even more important for me later. However, don't assume because you're working for a startup that you need to get paid nothing. Startups fail, and if that happens all you're going to have in your pocket is the cash. Trading experience for food is a little less convenient.

I started working. It was hard and I was in the deep end. I bought some experience to the table that they didn't have at that point, and I got my first sales experience, which I hated. I hated project management less, but what I really loved doing was development. For the work we were doing, development was quite light. The hours were long, and we hired devs, predominantly in India, to do configuration. The projects stretched out, often because I hadn't communicated with the customers well enough, and because the customer's expectations were not aligned with ours/reality.

3) Understand the customer

We were working for small businesses. This meant that a small amount of money meant a lot to the customer. The level of technical understanding of the customers was also low, which could be either extremely positive (importing csvs sounds complex and don't worry if it takes a month) or extremely negative (why can't you spell check e-mail addresses automatically). Additionally, in the end we were working for Salesforce. They didn't care how long it took us, they wanted the customer satisfied so they could get that sweet monthly SaaS payment on into the future. All this lead to extremely drawn-out projects, because that's what our customers demanded. That meant long hours, and lots of anger.

4) Understand the competition

I think this was the most crucial thing I didn't do. In the small business space for Salesforce, companies rise and fall all the time. I think this is due to the volatility of the customer type. It seems like the success strategy for companies in the space is to move to the medium-customer segment, effectively leaving the small businesses behind. I honestly have no idea if that was our strategy, but I probably wouldn't have joined the company if I'd realized how fraught with risk our market was. I even had another friend who had worked in the space, and shut down their company. In the end our competitive advantage seemed to only be how high our customer's expectations were in the sales pipeline.

5) Evaluate perks versus effort

If something goes wrong and you have to work until 3AM (and it will and you will), a bottle of expensive vodka is still less expensive than your hourly wage would have been. Is an office pet and an open bar worth the time you're spending at the office? Ask yourself this question often, because you'll be spending a lot of time at work.

At this point the pipeline was getting totally stuffed with old projects that had been drawn out for months because we couldn't deliver on our promises. Our desire and need for new deposits still grew, however, and so the pressure continued to build. The sales director was restless with this. I had been so excited at the beginning of the company to help design our processes, but we continually revisited and redesigned them, so much so that I think we went through 4 different visual designs for customer quotes in the 6 months I was there. I didn't think this was normal, and I felt like we needed more stability.

6) Remember that X% of $0 is $0

As the company became more fraught with drama, all the non-founders (there were now 6 in the company) were offered equity in the company. The first issue with this was that the company was surrounded by a bunch of other companies with different names, so we had no idea where the money was going. The second issue was this was a verbal agreement from the sales director. At this point I decided to leave the company.

I don't think there were any other lessons to learn, and I think I came out of the experience as a better person. If I'd turned down the offer I'd probably be reading Hacker News all starry eyed thinking startups were the promised land. They aren't, but they are fun, and I'd recommend everyone try them. But, protect yourself. Ensure you know what you are getting, and be realistic about the outcome at all times. If you are living hand-to-mouth as a college grad, don't rely on a successful exit as your savings plan.

In the end, I went crawling back to my old boss, but he hired me full time without an interview, and offered me more money! Taking into account my unpaid overtime, I got a 100% pay rise :). I was hurt by the experience, and the startup had threatened to call the cops if I didn't return my laptop and phone on the day I left, but looking back on it now, what a laugh! I felt taken advantage of, but I got valuable sales experience, learnt more about working with external devs (although I'm still not great at it), a chance to design processes for a company from the ground up, a better nose for bullshit and a few expensive bottles of vodka! It was an exhausting six months.

After I left, the founding CEO got f@#ked out of the company by the sales director, and then the sales director got f@#cked out of the company by the new CEO. The equity never materialized. The best story is of the other PM, who managed to score two medium-size enterprise clients for himself, and now earns six figures and works only a few days a week!