I’m on an Acela train between Boston and New York (listening to Boston’s More Than A Feeling – how recursive) on my way to the TechStars Boston 2010 Investor / Demo day.  I wasn’t able to make it to Boston yesterday for the Angel Boot Camp as I was running around NYC with the CEO of a company I invested in last week introducing him to a bunch of potential customers and partners. 

It sounds like Angel Boot Camp rocked.  My long time friend and co-angel investor Will Herman wrote a post titled Angel Investing that summarized some of his advice.  Will is finishing up his 31st angel investment (we’ve done a bunch together – including my very first one – NetGenesis in 1994) and he walks through what he’s learned from 16 years of angel investing.  Don Dodge also has a great post up titled How to be an Angel Investor…and make money.

Pitching your startup to investors is a deeply personal matter.

More often than not, they –– politely or not –– call your baby ugly. And that hurts. Good founders, I think, learn to not take the criticism too personally.

But in the end, it is personal. They are judging you. And your baby. Thumbs up, or thumbs down. 

And such is life. But how should we, as founders, judge them? Not all investors  are created equal, after all.  Once betrothed, the investor –– unlike the entrepreneur –– is unfirable, a step-father to your newborn startup, an undivorceable spouse in an epic marriage.

Like any proud founder, I am extremely protective of my newborn startup. She's my motherfucking baby, after all. 

Now, I don't claim to have years business knowledge or even necessarily have it right –– I'm doing this for the first time –– but I do have my own formula.

Its no surprise that most angel investors are successful entrepreneurs. You can see that in the list of names belowJeff Bezos, Reid Hoffman, Marc Andreessen, to single out a few. But are they as successful in the role of angel investor? Bloomberg BusinessWeek asked researcher YouNoodle to analyze the investment track record of this group of well-known tech personalities whose activity as angels has stayed largely hidden until now.

Click column heading once to reorder from highest to lowest. Click twice to reorder from lowest to highest.

2010 Rank	Investor	Number of Angel Investments	Percent of Companies Operating, Acquired, or Public (not dead)	Number of Employees*	Amount of Funding Received (in Millions)*	Best Financial Performance** (Rank)	Most Influential*** (Rank)	Most Diverse Portfolio**** (Rank)	Investment focus
1	Chris Dixon	23	100	3,283	1,071.8	1	11	1	B2B internet services, Consumer Internet
2	Ron Conway	190	97	29,703	3,407.0	2	1	12	Consumer Internet, Mobile
3	Reid Hoffman	49	96	69,796	2,270.9	4	3	24	Consumer Internet, Social Networking, Gaming
4	Esther Dyson	60	98	5,357	480.5	3	16	25	Consumer Internet, Social Networking, Space Exploration
5	Peter Thiel	26	92	69,499	1,577.4	8	2	9	Consumer Intenet, Mobile, B2B internet services
6	Marc Andreessen	53	100	3,835	1,157.6	6	6	20	Cloud Computing, Virtualization, SaaS, Consumer Software
7	Jeff Bezos	18	100	21,028	482.9	5	12	16	Online Marketplaces, Space Exploration
8	Chris Sacca	31	94	593	296.4	16	9	6	Consumer Internet, B2B Internet Services
9	Mike Maples	39	97	3,377	522.6	13	13	8	Consumer Internet, Mobile, Gaming, Retail
10	Andy Bechtolsheim	49	100	31,184	954.8	12	8	19	B2B Internet services
11	Paul Graham	129	84	606	84.4	7	14	21	Infrastructure, Virtualization, Networking
12	Max Levchin	7	100	491	277.5	21	4	3	Consumer Internet, SaaS
13	Aydin Senkut	65	95	933	316.8	9	21	11	Consumer Internet, B2B Internet Services
14	Bill Joy	24	100	5,275	551.1	20	7	7	Consumer Internet, Mobile, B2B Internet services
15	Kevin Rose	12	100	369	229.4	14	19	10	Networking, Infrastructure
16	Dave Duffield	18	89	2,271	219.9	10	15	22	Consumer Internet
17	Andrea Zurek	26	92	1,767	77.8	15	24	5	Consumer Internet, Search, Software
18	Marc Benioff	9	100	74,891	133.4	17	22	4	SaaS, B2B Internet Services
19	Jeff Clavier	52	92	911	276.2	22	5	17	Consumer Internet, B2B internet services
20	Caterina Fake	6	83	77	35.7	24	20	2	Consumer Internet, E-commerce
21	Martin Varsavsky	28	96	2,078	302.5	23	10	15	Consumer Internet
22	Naval Ravikant	21	90	308	187.3	18	17	18	Consumer Internet, B2B Internet Services
23	Joe Kraus	5	100	680	160.0	11	25	23	Consumer Internet, SaaS
24	Eric Schmidt	9	100	129	97.4	19	18	13	Enterprise Software, Consumer Internet
25	Lauren Flanagan	23	96	257	50.5	25	23	14	Healthcare & Biotechnology

^*Figures are total for all companies in the portfolio.
^**Annual growth of investments, companies operating at valuations above $100 million, and the sale of any companies for over $50 million.
^***Co-investment connections reveal how many angels they have worked with, uniqueness of co-investments, and critical bridges between angel groups.
^****Range of industries and countries in the angel's portfolio.

Data: YouNoodle

I’ve seen a number of situations recently that are something like the following.  A VC firm signs a term sheet with an early stage company. Let’s say it’s a $2M round.  The VC and entrepreneurs decide to set aside $500K for small investors (individual investors or micro-VCs). Because it’s a “hot” deal, there is way more small investor interest than there is capacity (the round is “oversubscribed”), and the entrepreneur needs to decide which investors are in and which are out.

The most common mistake entrepreneurs make is to base their choice solely on the investors’ “celebrity” value (by “celebrity” I generally mean in the TechCrunch sense, not the People magazine sense).  Picking celebrity angels might help you get a little more buzz when you announce the financing and a few SUL tweets, but that’s about it.  A startup is a long trip — what you should care about is whether, through the ups and downs and after the buzz dies down, the investors will actually roll up their sleeves and help you.

That isn’t to say that being a celebrity and being helpful are mutually exclusive.  Ron Conway is a celebrity (in the startup world) and is one of the hardest working investors I know. But there are other celebrity investors who I’m a co-investor with in a few companies who literally don’t respond to the founder’s emails.  And these are successful companies where the founder sends them only occasional emails about really important issues.

The second biggest mistake is picking angels that benefit the lead VC.  A lot of times when VCs guide entrepreneurs to certain investors what they are really doing is “horse trading” – they want you to let in so and so, because so and so got them into another deal, or will help them get into future deals.

It’s also smart to pick a varied group of people.  If you want a few celebrities to create some buzz, fine.  You should also pick some people who are connectors – who can introduce you to key people when you need it (varying connectors by geography and industry can also be helpful).  Also very important are active entrepreneurs who can (and will) give you practical advice about hiring, product development, financing etc.

Finally, don’t spend too much time agonizing over this.  One particularly silly situation I was involved with was where the CTO had invited me to invest but then the CEO decided he wanted to put me through multiple interviews before he’d let me in.  He probably spent a day of his time deciding whether to give me some tiny fraction of the round. Eventually he dinged me because I wasn’t famous, but at that point I was frankly kind of relieved since the CEO seemed to have such a bad sense of how to prioritize his time.

Disclosure: This post is entirely self serving, as I consider myself a non-celebrity but hard working small investor.

Chris Dixon is Cofounder of Hunch. He's also an investor in early-stage technology companies, including Skype (acquired by eBay), Postini (acquired by Google), Flarion (acquired by Qualcomm), Gracenote (acquired by Sony), P.A. Semi (acquired by Apple), Celtel (IPO), BladeLogic (acquired by BMC), TrialPay, Gerson Lehrman Group, ScanScout, OMGPOP, BillShrink, Oddcast, Panjiva, Knewton, and a handful of other startups that are still in stealth mode.