I received the following question earlier this week. It’s conveniently timed, as I recently participated in two angel investments – each with one of the structures defined below. What’s the best/preferred structure of investment money pre-VC investment. We’re in the beginnings of raising angel capital (~500k) and were wondering what, if any, considerations we should make regarding the investments to allow for VC later. Should we take convertible loans or issue straight preferred stock? What are the other options that are out there for investment structure? Is it too much of a hassle to handle future investments when there is an “angel group (say 5 doctors banded together)” versus a singular angel?

I’ve been very busy the past few weeks so I haven’t had much reading time. I’ve been slowly working my way through Company by Max Barry. Tonight, after my friends left our condo at Beaver Creek after our Friday night sushi orgy, I laid down on the coach, near the fire, across from Amy, and finally polished it off. Company was brilliant. Imagine a novel about a Dilbert-esque company run amok, with extraordinary character development and a steady build-up to a 24–like plot twist. I found myself laughing out loud regularly, which is always a good sign (although it means you probably shouldn’t read this book on an airplane.) The author – Max Barry – claims to have “spent the best years of his life in the bowels of Hewlett-Packard, conducting secret research for this book.” He did a good job.

I spent the requisite five minutes on Google Pages tonight now that I could actually log in. I created a very simple page, just to see what it felt like. I’ll poke around some more when I’m bored, but for now I still don’t get it. I do, however, really like the Google single sign-on which seems to have automagically appeared. My Google services are getting a little more tightly integrated which is a good thing. Hopefully the spam bots won’t figure out the algorithm for determining gmail addresses from the Google Page address (duh – very easy – nah – wishful thinking.)

Ah – a second great quote from Hickenlooper this morning for those of you in the audience from Colorado. John just said “Denver Is Nothing Without Boulder.” When I first moved here in the mid-1990’s, Boulder was definitely viewed “snidely” by many people in Denver, especially in the business community. It’s great to hear the Mayor of Denver thinking about the region, rather than just the city that he’s mayor of. Denver (and Boulder) are lucky to have John as Mayor.

I’m at the Venture Capital in the Rockies Conference today. Denver’s awesome Mayor – John Hickenlooper – is the breakfast speaker. It’s 8:25 and I’ve already heard the quote of the day. John – who is an entrepreneur – is talking about his entree into politics. When he mentioned to his brother that he was thinking about running for mayor, his brother responded, “C’mon John, politics is hollywood for ugly people.” Perfect.

Matt Blumberg – the CEO of Return Path – wrote a post on a meeting he hosted yesterday with some of the old-timers at Return Path – including one of the founders who is no longer at Return Path – to explore reinventing Return Path’s original business (ECOA – email change of address.) Return Path – which was founded in 1999 (I invested in Veripost – the “other” early ECOA provider – in 2000 which was merged with Return Path in 2001) was originally based on being “the” ECOA provider. At the time, we convinced ourselves that this could be a very big business. We were wrong. ECOA is a small business that can be run profitably, but it’s not enough to build a VC-backed company. Fortunately, Matt and team determined this early on (in 2002) and started aggressively expanding Return Path’s footprint in the email services market – both through organic growth and acquisition. Today Return Path is a medium sized company (e.g. big enough to matter and be considered a real company), growing quickly, and a leader in several market segments (oh – including ECOA).

I don’t understand, but that’s nothing new. I saw the rapidly expanding buzz about Google Page Creator and went to check it out. We were investors in Geocities and this immediately reminded me of – Geocities. I logged in, went to change my template, and got the following message: Thank some-diety that it’s “not because of anything I did.” What a trip down memory lane. I guess it’s beta, but I still don’t understand.

So – Jonathan Schwartz – Sun’s President – blogged about Sun’s offer to let people try a Niagra server free for 60 days. According to Jonathan: The program started off slowly – partly due to internal disbelief (there’s a long story, there), but secondarily, our focus group feedback suggested no one believed we’d actually send them a free Niagara. So let me reiterate: go to sun.com, fill out the form, we’ll send you the fastest server on earth, absolutely free. If you don’t like it, we’ll send someone to pick it up.

I woke up this morning feeling like brogging about a few of the companies I’ve invested in. It’s easy today since they are announcing meaningful customer implementations which are a very good thing for a young company. I already talked about NewsGator Enterprise Server and Law Firms; next up is Oxlo and GM. Oxlo announced that its product has been implemented at six dealer service providers with integration in the GM Retail Inventory Management (RIM) implementation. This is a key integration for Oxlo as they are now “in production” with GM. RIM is a sophisticated bi-directional real-time integration between GM and their Dealers – this integration enables GM and their Dealers to more efficiently manage parts inventory at the Dealership – saving both GM and the Dealer inventory expense in the process.