In talking to a bunch of companies and signing some up and turning some down (either by me or by them turning me down), I have determined the sweet spot for team size at which it seems to maximize my participation.
It ranges from one and maxing out around 10 or so.
Why is this so?
I find that in my areas of contribution (User experience, Product strategy, Online advertising, etc.) I can make the most impact if there is not someone there at the moment covering that area. While in my role as advisor I do not get on critical path by actually doing the work, I help give them direction on hiring, what they need to do, developing their strategy (in all those areas), and give them an expert to bounce things off of. One goal I try to set for myself in my advisor term is to find resources, internal or external, to replace whatever functions I am advising on so that by the end of the term, they have support in those areas.
I have found that if companies already have people covering that area, then my impact is much less. It also is difficult for company personnel to envision how to integrate my help as well. For example, if there is already a GUI person there, then does it justify giving me my advisor compensation to just be a evaluator of what that GUI person does? For things like GUI and product strategy, it is difficult to express your opinion AND make the team members internalize that thought enough to be able to take it further. And, if you are not an employee and not there 24/7 to drive a direction, it becomes really tough to make that direction stick when someone else is already working on it, and has their own opinion on how things should be done.
That is fine. I do not take this personally. I think that if a company already has support in that area, then that’s perfectly fine. I don’t want to get into a situation where I am constantly butting heads with already present resources.
By the time a company reaches approximately 10 people, typically many of the areas I would help on are already covered. Time to move on to the next company where I CAN make a large impact…

I consistently hear this now. Suddenly engineers, GUI folks, and online sales people are scarce.
In the last few months, many new startups emerged. I guess they snapped up all the good engineers because now it seems that everyone has moved somewhere and is planning to stay there for a while. This is why I am trying to make contacts in outsourcing overseas for engineering.
GUI people did the same thing and switched jobs, although most of the ones I’ve heard of went to larger companies. In my experience, GUI people tend to be more conservative. Not sure why. I haven’t seen many take the chance of joining an early stage startup. Many startups have told me stories of failed attempts at hiring a GUI resource on staff. They turned out to be not that good, not experienced enough, or just out of school. I had to go create my own list of GUI design shops and resources, and keep track of everyone who is consulting.
The real scarce resource is online sales folks. The really good ones are truly hard to find. I feel fortunate that I got to know a ton of them at the best training ground for that: Yahoo!. Many of them have moved on, but mostly to higher positions/pay elsewhere. Here’s the kicker: to lure them away sometimes requires a lot of tinkering with compensation. For early stage companies, that’s really tough because they don’t have a lot of cash. I am now trying to see if some of the few out there are willing to consult. Some of them are actually thinking about it thankfully. About every early stage company that is thinking of selling advertising has no experience in this area and certainly no contacts at all. It’s one of the most valuable things that I can do is connect them to a truly good online sales person.
Time to get creative in finding ways of solving this personnel dilemma….

This week saw the convergence of a few deadlines in financing and me going out of town. Landing in NYC, I realized I didn’t own a fax machine and I needed to sign some documents and fax them.
So out I go to the nearest Staples Express, plunk down $150 to buy a brand new Brother multifunction wonder, and then proceed to carry the huge box back to my apartment.
A few sweaty minutes later, I get to my place and set it up. I plug it all in and thankfully after a few tests, it all works fine.
I then sit down to print out a whole bunch of docs and prepare them for faxing to various places. What a big time suck. I need to sign two agreements and create fax cover sheets for both of them. I proceed to print out tons of paper and lay them out on my table and double check what they are and where they’re supposed to go. Finally I get that all organized and sign them, and then stuff them into my fax machine multiple times as many people need to have copies of them. I also create another fax for my financial person with wiring instructions, sign that, and then fax it away.
It seems as though the point at which all this is broken is the signature.
I can already email things around. I use Acrobat to generate PDFs all the time so I know that the docs won’t be altered. That’s not the problem.
The problem is when I need to physically sign something. Then I need to print something out, sign it, and then get back into an electronic state. This is typically a fax machine, but it can also mean scanning in of the doc and turning it into a PDF before emailing. Scanning this in can be problem. I have a Fujitsu ScanSnap seems to work most of the time, but if the paper is even slightly bent, it starts screwing up bulk scanning. Somehow, fax machines seem more resilient in feeding less than optimal paper, but I have to fax it somewhere. A buddy of mine told me to sign up for eFax which I finally am paying for now. It is about $170/year, but it definitely works great and now I have a fax number to boot. When faxes come in, I set it to convert to PDF so now I have electronic versions of all my faxes. I can also fax myself so that it essentially becomes a scanning->PDF solution.
But how can I insert my signature electronically? I suppose I could scan my signature into an image and then copy/paste it into documents. Security-wise, that isn’t too great; as soon as somebody gets hold of that image, I’m toast.
Where are all the digital signature solutions? I used to hear talk of companies attempting solutions but I don’t hear much about them now. A business opportunity perhaps, in the world of Web 2.0+?
Going paperless is key; it seems ridiculous that one of my most favorite appliances is my paper shredder. When we talk about legal documents, we’re talking about pages upon pages of formal wording that I have to go through and it sucks to carry it around, only to shred it when I’m done. Finally, I am starting to get used to reading these docs on the PC screen, although sometimes I find it still difficult (thank god for the ability to print 2 pages onto one piece of paper through MS Word). I have (almost) gotten my entire financial life to go paperless. Somehow, the world of signing agreements needs to get there as well.