Help me trust collaborators

Story of a first-born who works alone maintaining a world-wide online booking platform.

Yes, this post is about me, but what I would really like to know is whether there are other people in my same situation out there and how they worked it out. But let’s take it slowly and explain better:

I like computers, always did, and I've always been self-taught since when I was six, when I coded my first script in BASIC on my father’s Intel 8082. I started working during school, when I was sixteen,as a freelancer for a web company, providing their customers with dynamic applications on their websites. This web company picked me up because, they said, they were not able to find a good web programmer worth to be employed full-time (we are talking about the early 2000s).

Then college came, I chose Computer Engineering confident it was the obvious thing to do. The result: I left college after five years of me trying to fight “all theory-zero practice” professors who confused “=” and “==” operators and insanely sciolistic Chemistry exams (yes, in a CE course). Oh, and how can I forget my wonderful colleagues who played cards and read “Gazzetta dello Sport” (a popular sport newspaper) all the time, everywhere? Most of them knew or cared nothing about the knowledge we were supposed to obtain, they only thought about passing exams and that was all.

Things changed for me in the late 2008, when some people invited me to leave college and join a new born tech company; they would even give me shares for free and a monthly pay. So I accepted.

The goal was to build an instant online hotel booking platform, à la Booking.com, operating in a single south-east Italian state (the one I live in). And yes, I did it: reservations started to arrive and hundreds of hotels were listed in our website.

Things were growing very very fast: other people wanted to exclusively use our platform for some Italian and foreign destinations, so we adopted a franchising formula. As business was increasing, so was complexity: more software and logic abstraction strategies were needed, server administration tasks became heavier, technical support was suddenly a duty we couldn't avoid and design/graphics became a very important part of the platform.

Soon I realized I couldn't take all that load (who would?) and started to search for collaborators. I supervised tens of job interviews with hobbyists, new graduates and “experienced” people. Almost everyone were frightened by the complexity of our project and said they were searching for a simpler job. I eventually put some of them on trial but none of them seemed to be gaining confidence with our platform and workflow, even after a few months of work spent with me solving their problems. Totally a waste of time.

Now that our new long term platform is almost ready to be published after me spending days and nights working on it, I took some time to think about the whole story and started to ask myself why it is so difficult to me to find collaborators or simply to be satisfied with other’s work. 

Am I a bad team leader? Am I not good at training other people? Am I expecting too much from them? or… haven’t I just find the right people? Are good level collaborators, especially tech ones, really so hard to find? Do they really prefer to search for another simpler job rather than study hard and become better professionals?

Have you ever been in such situation? Would you help me sharing your thoughts? At least you, my reader,won’t you collaborate with me?

Maybe send me a tweet at @nicolopigna!