I sold my first company in 1999. We had a rapidly growing online catalog of business phone systems and related products and service (PhoneZone). In late 1998,

I sold my first company in 1999. We had a rapidly growing online catalog of business phone systems and related products and service (PhoneZone). In late 1998, we got a term sheet from a well known VC. The terms were ok, except it was clear they wanted to replace me with a "seasoned" CEO, who I expected would push us aside and build a top heavy organization. At the same time, I had a chance meeting with the founder of Hello Direct, a successful and public catalog retailer of similar products. We got an offer to sell in the low millions. Chump change right? It was pretty clear by then the dot com bubble was out of control and that things were going to end badly. I decided it was better to take some money off the table and join HD, since they'd probably do just fine. Turned out to be a good decision. I was able to buy a house, and got through the crash just fine. If we had tried to go all the way, I am 99% sure we'd have burned through our funding and crashed and burned in 2000, and ended up with nothing. Like anything in life, whether to sell or not depends on the situation. In retrospect, I wish I could have kept PhoneZone as an independent company. It would have been a great business long term, but I don't think it was in the cards due to forces beyond our control. So no regrets.