Things learned while running your own self-funded startup

Trying to get funding is described as "soul sucking" even by Paul Graham and in our experience this is a startup killing move. Very few people talk about mental health for entrepreneurs and for us the most challenging times was talking to investors. If a constant stream of people told you, your business was not worth spending time or money, after how many rejections will you start doubting your company and even yourself?

Investors asking for a stream of documents, asking us to drive down for partner meetings, arriving late at meetings, un-responsive to emails: They all take a toll on the startup and more importantly on entrepreneurs.

Getting funded is a rat race. You get the money and then clock starts ticking for sales, series A,B,C , 10x the returns etc.

The startup newsletter are full of wins, and VC fundings and "we are killing it bro" mentality but how often do we stop to talk about those that failed?

I always find these perspectives and retrospectives useful and interesting. Different people always point out different things, because everyone's business is at least slightly different in one respect or another. (be it funding, customer base, product scale, product type, employee count, number of concurrent projects, how successful they were, etc.)

For example, the book "The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers" by Ben Horowitz provided good insight into managing larger tech companies and was enjoyable to read.

- The amount that they will try to squeeze you and give you the runaround is highly dependent on the personalities and the resources of the team that you’re selling to; it’s not generally consistent across the entire company, unless you’re dealing with a central purchasing department (hopefully you’re not, except for processing your PO). Of course, it also depends on the amount of value that your product provides compared to their current or potential internal solutions, as well as your competitors.

- Getting paid promptly is much easier if you write your contract with milestones and require receipt of payment for a previous milestone before work on the next milestone begins. Invoice in advance so the “net 30” expires on the day you want to be paid, or demand “due upon receipt” terms.

Blindly signing subjects you to potentially nasty term, and obligated you not to talk about certain things. This in turn can be used as leverage by the other side if things go badly.

Really, it's just don't blindly sign any agreement. Unfortunately agreements are so ponderous (clickwrap) that most people are used to doing that