Ask HN: Any desperate things you did just to keep your startup alive?

I coached tennis for some extra money on the side.

I paid per milestone, which were set by the developer according to his own estimation of delivery, with a thousand dollar plus bonus to meeting his own schedule. there was never any dispute, just the occasional 'I'm sorry this has taken so long, something came up' until after getting paid for near completing the first three milestones, he disappeared.

I was in another continent, so after all communication failed, decided not to peruse the matter. However I ran into him at PyCon this year, about 2 years afterwards. I didn't say anything, as to not cause a commotion. I'm over it, and a lot has changed in my life since, including that I can now do all the work I once needed him for.

When I started my first software related company at 21 (almost 3 years ago) I had already had some small successes in other businesses, and had a fairly strong customer base to start because of contacts I had made. So I went out hired employees bought copy machines, set up an office etc. But after the 6th pay period (3 months in) I paid all my employees and I had $3.62 left in the company bank account with several unpaid invoices from clients who I did not know very well, since we were working mainly for law firms and they are famous for not paying in a timely manner I did not know what to do.

I went and took an evening job at "geek squad" for $13 hour and started selling cars at a friends car lot on the weekends in a city about 50 miles away so none of my employees would know we were struggling. Often times over those next few months I was paying my employees from money I had earned working those two jobs which none of my employees even knew I had.

I eventually started researching effective ways to collect past due bills and I was harsh and even lost a few customers in my collection tactics, but ultimately learned a great deal about the types of customers I did and did not want which allowed me to realize that having tons of business was not necessarily as good as simply having a smaller, loyal customer base who pays their bills and respects your work.

I can recall one conversation where I was speaking to an attorney's secretary and she told me that after talking to "John" Aka the attorney in question, he simply did not have the money to pay the bill, but he "would get it paid as soon as possible" to which I quickly popped off "Well why don't you tell John that if he doesn't have the money he needs to stop parking his Aston Martin in front of my office."

luckily for me, my young hot headedness paid off and I received a hand delivered check the very next day.

While I struggled for some time to come and eventually spent my entire savings paying my employees salaries the business did eventually succeed and go on to be very sustainable.

When selling the company to a large firm out of Charlotte, NC I was even able to negotiate terms allowing all my employees to keep their same grade of pay for at least 2 years after the sale (they were all on salary and paid above market rate) While I worked harder in those 19 moths than I ever had in my life it was the most fulfilling time that I have ever been through and it shaped the me into the person I am today.

saw the stream of your talk at MIT recently. good stuff.