I have a friend helping out his friend's startup. We'll say Joe is helping out Rick with his party finder app.
Joe has known Rick for many years, and Joe is pretty well into his technology career. Rick has built a small tech team, but has received advice from Joe and a lot of encouragement from Joe. Included in this, Joe has forwarded Rick to a startup program that netted him $20k in free advertisements. This is just one example of how Joe has tried to look out for Rick.
Joe has his own software company but it's been much harder to get lifted when compared to an app company. After hitting half a million downloads, Rick was having an easy time getting investor attention. Around this time, Joe offered an investor database to Rick for a small pricepoint. Rick did a 180 and asked Joe to help deliver user data to his paying enterprise customers. Joe did this but quickly found territorial behavior from the existing tech team when it came to getting access and getting the job done without having his credibility questioned (why?). Rick's tech team was not very experienced and was on the fritz about handling user data from a variety of perspectives. The job didn't go so well since Rick's lead technical person felt it would be quicker to do the job himself (miscommunication). While trying to be simply helpful, a lot of this business inefficiency started to dump back on Joe. Joe was literally accused, asked to answer for, and made to sign a memo stating he did not steal data from Rick's database (wtf?). After all this, Joe frustratingly told Rick that his tech team was lead by a moron (apparently) and he could check the logs any time to see how ridiculous this all was sounding. Rick then asked Joe for a second proposal, this time working directly with him.
Joe wants to run in the other direction. Joe really needs the cash, however. What might be a quick pro/con of working with a friend who is paying a fair market price but might be unapproachable or unable to hear the realities of his business "internally"? What are some stories you have as a technical person digging through to the realities when dealing with a CEO point-person who is amidst pitch sessions and organizational motivation? Is the ego of a pitch-man delicate, or how can someone best support a friend while in the month(s) they are pitching?
Generally speaking, was a mistake made by Joe for engaging with Rick because it had the subtext of friendship and not business? Are startup teams territorial to outsiders that have a preexisting relationship with the C-Level? Is the experience of coaching a friend toward success transferable (i.e. through financing support, systems architecture, etc.) and what are some stories you have of using such an experience to formalize an advisory practice?