Raising Money from Angel Investors

I just returned from a 128 Innovation Capital Group meeting at a hotel on Route 128 in Boston. Turns out that I had attended one of their sessions more than ten years ago when raising money for my last startup WebOnTap, Inc. I know this because when I showed up at the venue my nametag had the WebOnTap name on it instead of my Augmented brand - a company name that hasn't existed since my partner and I sold the company to Endurance International (nee Bizland.com) back in 2000.

I used to attend a lot of these back in my earlier startup days, and I was struck by a few interesting things.

• The average age of the attendees was at least 20 years older than I remember. Maybe it was my personal myopia at the time, but I could have sworn that the majority of folks in attendance in 1998 were people in their late 20s trying to start the next Ebay and hustling for money. That was at the height of the dotcom boom, of course, so I'm probably somewhat correct in my recollection. This event was much more mature (literally). For proof, during the "stand up and introduce yourself for 15 seconds" part of the meeting virtually no one exceeded their allotted time. Remarkable - I remember that little exercise taking *hours* back in the day.
• Presenter Chris Sheehan (a managing member of CommonAngels, an angel funding group in Boston) laid out a process for approaching angels that had changed little since I last paid attention. The big difference was that Mr Sheehan acknowledged that initially getting in front of angels was almost always a function of working a personal network, and not of a compelling plan, per se. This was true last time I tuned in to the process, but Mr Sheehan acknowledged it up front this time.
• I was also struck by the fact that there seemed to be many more angel groups out there than I recall, and that most seemed to have their act together. Last time I was involved in that world, angel groups almost didn't want to tell people that they were out there, let alone how to work with them (probably to filter out all the dreck that they were getting). I'm sure they get dreck now, but either less of it or they're better at screening after submission.

The entrepreneurs I spoke with were familiar, of course. Enthusiastic, starry eyed by the enormity of their ideas, and talking way too fast - probably because they were afraid I'd lose interest quickly.

For the record, I met Van Garrett of allmealdeals.com - a fascinating concept where small restaurants can offer short-term promotions on meals, which can then be distributed to you via Twitter or SMS (I'm now a subscriber). Tai Chan of Smargineering.com was pitching a novel mobile payments system, and Dave Belfer-Shevett was putting together the company around a homebrewed conference attendance application he's designed. It felt like old times.

But in one way it was markedly different: I'm not raising money. For me, this time, I didn't have that sense of tension and pressure that comes from having a payroll to meet or rent to pay or a pilot marketing campaign to get out the door. I may get back and do that again, possibly soon, but for now I got to sit back and watch without any real agenda - just interesting people and interesting ideas.