This brings back very uncomfortable memories. When I was 25 I was helping a friend who was creating the first structural analysis software for the PC. I introduced my friend and his partner to this strange guy in Dearborn, Michigan. There were meetings at the airport and in his office in Dearborn. This guy claimed to be a wizard at arbitrage and arcane financial instruments. He said he worked out all the algorithms for Ford Motor for hedging copper futures. He was overweight, had greasy hair, and, I kid you not, his back pockets were usually turned inside out. We figured, eccentric genius. At least at first. All he ever provided were excuses. He was waiting to flip some sort of bond issue overseas that would give him $10 million, etc. That business never got off the ground.<p>Then a year later my own partner and I got a call. We had been looking for a manufacturing business to acquire. The crazy guy had a contact in Chicago who was looking for an operations team to come in on a deal to acquire a manufacturer of audio mixing boards. This company was still run by the founder who had practically invented the industry. There were 50 employees and customers included major studios and venues around the world, including the US Senate and the Kremlin. The deal maker, lets call him DB, proposed that each of four partners -the founder, me, my partner, and him- put $25K into a holding company. He would arrange a $250K line of credit from the Korean bank in Chicago that he was friends with. Then we would operate the company out of bankruptcy. Well we three each sent him $25K (my dad lent me the money). We did all the legal paper work, and I showed up the next day as one of the new owners of a $3 million/year company. Very exciting for a 27 yr old. To make the story short. DB was a complete crook. He needed $75K to pay off someone else he had screwed and was threatening his life. The business shut down. 50 people lost their jobs. It took me years to get back on my feet financially.
The Valley has been filled with these types since it became known for loose money and fame. I've met perpetual VCs without money, Founders with no real startup other than a logo and domain name, and name-dropping nobodies since they first day I came here.<p>In general be suspicious of flakiness and an inability to meet any agreed upon timeline, and always validate information in person when possible. Even if they are real and show these attributes, you likely don't want them involved with your business ventures anyways.
<i>None of these questions or tactics will be offensive to real angel investors. In fact, they will give the real ones more confidence in you.</i><p>This is a big sticking point for first time founders because it by definition turns the tables and now the founder is the one who is challenging the supposed expert investor.<p>This can be tough for people to do if they aren't used to it.
What a fascinating story. Thank you for sharing it.<p>I totally hear you on fact that it was hard to see at the time, but obvious now. You want to believe, which completely messes with your mind.