The other week I spoke and mentored at The Lean Startup Machine in New York, which was a ton of fun for everyone involved. I had a young entrepreneur come up and ask me an interesting question:
“What was the #1 lesson from each of the companies you have been involved with?”
It is always hard to pick just one, but I thought it was a great question and interesting exercise. Here is my first take at an answer:
Trilogy Software (enterprise software, marketing): if you are solving a real need, you can often charge more money than you think — don’t be afraid to rock the boat and push the envelope on pricing.
Broadview (tech M&A, analyst): If you really want to impress someone, obsess about the details.
Envive (enterprise software, sales): don’t involve the CEO in a sale too early, but keep him/her in your back pocket as a final closer for tough deals. Reason: this allows you to play “good cop” during negotiations leading up to close, and at closing time, involving the CEO both makes the customer feel important and means snap decisions can be made right then and there to close a deal without delay or second-thoughts.
Ithority (bootstrapped Internet 1.0 company, sold to Opus360; founder/CEO): build relationships with strategic buyers early and, certainly for early-stage companies, do not delegate this task.
Opus360 (Internet, VP Bizdev and very involved on product side): the best motivator for a sales team is money, but the best motivator for a talented product team is pride.
Electric Sheep (virtual worlds / games, VP Bizdev and VP Product): this one really is a tie between “focus is critical, no matter how much money you have raised” and “don’t raise money from strategic investors until at least a series B”
Aprizi (consumer Internet, founder/CEO): I think more time is needed before I have the true answer. For those who don’t know yet, after a year of pushing on this concept, we have decided to wind Aprizi down. I have a longer post coming where I try to analyze our path. Right now, I will say that Aprizi gave me the chance to put “lean startup” concepts to work and made me a believer. I will also say that “ground-floor startup” and “having a family” can mix, but it is brutal, and it may be better to nurture and iterate something part-time until it shows real promise than to chase a vision from a standing start.