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Hi, I’m a tech VC on Twitter. I’m @xyzvc

My icon is cool.  It’s a painting/cartoon/wacky photo.  Shows that I’m hip and approachable.  But when I meet with you, I’ll still crush your dreams. 

I tweet about technology, but occassionaly post personal stuff.  Important to show I have a sensitive side and care about more than just making tons of dough. 

I use # tags, sometimes as a funny form of emphasis.  Kind of like a wink and a smile ;) #donttakethisposttooseriously

I love Twitter because I can broadcast my blog posts.  Otherwise, no one would read them!  I blog at xyzvc.com!

I tweet blog posts with advice on fundraising, customer acquisition, and company building.  Usually, someone really smart has said it before and said it better.  But I haven’t been in Hacker News for a while, so I figured there is no harm reinventing the wheel. 

Retweeting is fun.  It’s like a virtual high-five.  I retweet the posts of my partners, coinvestors, and entrepreneurs I’ve backed.  Oh, I also retweet posts from guys whose butts I’m currently kissing so that they will like me.  I really hope @fredwilson retweets this… I’d get so many new followers!

My portfolio companies are the best.  I will share so much of their good news with you it will make you want to unfollow me (unless you are a co-investor, in which case you will probably RT and add a #)

If a portfolio company is doing bad, no Twitter love.  It’s like going to Disneyworld and trying to find Hercules or Mulan.  It’s like they never existed.

I also tweet about the cool places I’ve been (via Foursquare and Gowalla), things I buy (via Swipely and Blippy), and the cool places I’m going to go (via Plancast).   

Wow, that’s a lot of tweeting! That’s why I also tweet about how busy I’ve been and how little I’ve slept. It’s a tough life. 

Full disclosure, I’ve been a tech VC and I’ve done most of these things. 

I remember early on in my VC career, I chatted with an entrepreneur turned VC who remarked “as an entrepreneur, time is your enemy.  As a VC, time is your friend.”

What I think some VC’s mean when they say this is that investors typically have limited incentive to move quickly.  Unless there is a forcing function like a competing term sheet, it’s usually preferred to spend more time doing diligence on an investment mainly to get to know the founder better, watching the company make more progress (or eliminate risks), and getting buy-in from others in one’s firm.

One of my current partners calls this “hanging around the hoop”.  It’s a good strategy in basketball, but I think it’s pretty lame as an early stage investor, and specifically at the seed stage. 

I was chatting with another successful entrepreneur today who is also an active angel investor.  He emphasized the high value he places on speed of decision-making, and remarked that being known for speed will lead to positive selection bias.

This is particularly true for repeat entrepreneurs.  Often, successful founders can fund the early stages of their company themselves.  But if they are going to raise outside money (to provide feedback, help, and leverage on their dollars), they are more likely to go to folks they know will move fast and make decisions on rational dimensions that will actually help the company.  They will avoid investors who hang around the hoop, or send entrepreneurs on assignments that aren’t truly productive.  The truth is all VC’s can make fast decisions if they need to, they just need pressure to be applied properly. 

It’s hard to force an investor to move quickly unless you create competition.  But what you can do is try to tell whether the VC is doing good vs. bad due diligence.  ”Good” due diligence doesn’t take up entrepreneur time, burn the time of their valuable references, and are usually productive towards the goals of the company.  They include:

1. VC’s doing backchannel due diligence on the team.  This is good practice as an investor, and doesn’t burn a lot of cycles for the entrepreneur.  Usually if the VC is reaching out to their own networks, it means that they care enough to burn the time of their own contacts. 

2. Introducing the entrepreneur to real prospective customers and partners and seeing if they can close.  This is very informative for the investor and entrepreneurs want to sell to good customers.

3. Introducing the entrepreneur to executives with deep domain knowledge in the space.  This is a real opportunity for the entrepreneur to learn and the person may end up being a valuable advisor or even a member of the team. 

4. Meetings with a purpose.  The investor and entrepreneur want to get to know each other better.  But these interactions should be structured and constructive.  Debate business models, discuss product priorities, interview the founders to understand their strengths and weaknesses… these are all good, but definitely have a purpose and prepare to dig in deep at a level that the entrepreneur finds beneficial. 

5. Quick “no’s”.  It’s counter-intuitive.  But if a VC gives a quick “no” but with a very clear reason that seems addressable, there is no better due diligence than seeing if the entrepreneur responds and comes back having addressed the issue.  It happens rarely, but if the feedback was genuine, responding to the feedback will create genuine interest.  

Bad due diligence looks like:

1. Calling all an entrepreneurs references just to go through the motions or for selfish gain.  This does happen a lot.  The investor may know they are very unlikely to invest, but they think person x,y,or z on the reference list is interesting, so they’d love to talk to them. 

2. Multiple meetings rehashing the same information.  Lame.  It’s part of the difficulty pitching to large partnerships, but you’d hope that an investor would sufficiently brief his team so that conversations go deeper each time into the critical levers of the business.  Not rehashing generic stuff.  Also, this is a signal that the entrepreneur is hanging around the hoop.  They are waiting to hear an update and aren’t prepared and focused towards driving to a decision. 

3. Making entrepreneurs fly to partner meetings when they aren’t extremely enthusiastic about the investment (particularly a danger for junior VC’s).  Total waste of time and money. The investor in this case is not only hanging around the hoop, they are trying to take the temperature of their partnerships to see if they should spend more time with you. Remember, junior VC’s get “credit” for perceived activity, so they are more likely to do this so their partners know they “saw” the investment even if they know it won’t get through the partnership. 

4. Doing due diligence to inform an investment in a competitor (obvious and happens a lot, surprisingly).

5. Lame introductions to irrelevant people.  Of course, VC’s can’t always assess what kinds of customer/partner/executive intros would be fruitful, but their ability to get close is a) a signal that the investor “gets it” and b) really will be able to help.  But when there is a generational/industry gap between an entrepreneur and an investor, you are more likely to get intros to random or ill-suited people.  For example, there has been more than one example of Boston consumer internet companies in need of technical leadership talent that got directed to really old-school enterprise software executives.  Those types of cases are a waste of time at best, and truly harmful to the business at worst. 

As an entrepreneur, it’s not always easy to tell whether the VC is doing good or bad due diligence.  Hopefully these signals help.  But I would say that overall, speed is a great indicator.  If they are making progress quickly, that’s great.  If it’s taking a long time, it means they are hanging around the hoop.  And this is what should happen to people who hang around the hoop. 

Valuations in venture backed companies seem to be a mystery to most.
Even in the past 18 months, when it was close to impossible to raise
money, we’ve seen valuations in early stage companies that caused a
lot of headscratching (Square, Foursquare, Groupon, etc).

It begs the question of where these valuations come ffrom.  B-school
students are trained to believe that valuations are driven by the
present value of future cash flows, which is a f(cash flow, growth,
risk, and capital structure).

But how does this hold when there are no cash flows (in fact, when
there is no business model)?

The answer is that vc rounds are priced by the market - by supply and
demand. I once met an experienced VC who admitted to me that he didn’t
actually know how to do a DCF.  But he did know where a deal would
likely close at based on pattern recognition.

Ultimately, the right way to think about VC valuation is not a finance
exercise but a negotiations one.   On the investor side, the goal is
to acquire as large a position in the company and exert as much
control as possible while keeping the entrepreneur sufficiently
motivated.  On the entrepreneur side, the goal is to maintain a much
ownership and control as possible while bringing in a helpful and
motivated investor. The bounds between sufficient entrepreneur
motivation and the potential to create an attractive return to an
investor is a very wide ZOPA (Zone of possible agreement).  Where the
deal closes is a function of the relative bargaining power of the
constituents.  In other words, are there many other Investors
clamouring to invest in the company (rarely)?  Do the Investors have
lots of options for where to put their capital (often).  To steal
another negotiations term - it comes down to having a good BATNA (Best
Alternative to a Negotiated Agreement).

Remember also that it’s not only about valuation, but a lot of other
terms that have value.  Liquidation preference, option pool, founder
liquidity, BOD seats, etc.  There are a lot of posts out there that
describe some of the levers Investors use to make up for higher
valuations.  Entrepreneurs should definitely read them.

Sorry for the typos, this was written on my iPhone.

I wrote a post on Sunday about Why the VC Business is like a big game of Texas Hold’Em. As folks pointed out, it’s not a perfect analogy, but there are major similarities because of the interplay of skill and luck and the advantage derived from early successes.

But here’s the reason this structure makes it difficult for new entrants in the business: Skill beats luck over time, but most new VC’s only have a few shots to prove themselves.  VC’s typically make only 2 investments each year, and newer VC’s (including both new GP’s and Principles) aren’t that productive early on.  At the same time, these investments carry a lot of weight early in one’s career.  ”You only have a couple bullets, so use them wisely” is the common advice.

This doesn’t really jive with the dynamics of the industry and kind of encourages risk averse, mainstream behavior.  Also, because success begets success, it sometimes allows folks who aren’t necessarily very good at the business to get out ahead quickly with a lucky win, and then ride the coattails of that success for a while.

Now, I don’t think there is really a realistic solution to this.  Startups take a long time to develop, and so it would be unrealistic to give a young VC tons to time to see if they are good over the life of a portfolio of investments.  Also, senior GP’s take a lot of other subjective signals into account when thinking about elevating a new VC to a more prominent position.

Still, something doesn’t quite sit right with me with the status quo.  In any case, it’s the reality and new entrants need to deal with it.  Having said that, I have observed some good strategies that seem to work for some of the up and coming investors I know.  Here are three that come to mind:

1. Make a lot of investments. This is a pretty smart strategy I think.  Since there is a lot of chance in this business, and it takes a long time for investments to mature, it behooves a new VC to get as many shots on the board as possible in a short amount of time.  This allows the benefits of a portfolio to take hold, and provides a decent possibility of a quick win.  The downside is that if a number of investments go sideways, it’s easy for your colleagues to make the case that you have no idea what you are doing.  Also, you could hit a really bad moment in the economic cycle that could crater a bunch of your companies.  

2. Be Different.  This is my favorite.  The reality that I haven’t mentioned yet is that not all VC’s have access to the same deals.  So it’s really not like Poker, where every player has equal chance to draw the same cards.  New VC’s have the deck stacked against them because most great entrepreneurs would rather go with a proven success than a new up-and-comer.  So, one strategy for a new VC to take is to be radically different from one’s peers in terms of the stage they invest in, sector, evaluation criteria, or some other meaningful vector.  It’s a difficult bet to make, and one that’s really hard in a partnership unless others buy-in to your contrarian approach.  But I think this can work. Take Y-Combinator.  When it started, a lot of VC’s scoffed and said that Paul Graham was investing in dinky little companies and buying tiny ownership.  But his approach was radically different, he attracted a completely different kind of entrepreneur, and seems to be doing pretty well.  Oh, but remember - Paul did this himself, he didn’t have to content with a partnership of VC’s with a different mindset, which gave him a lot of freedom to pursue his strategy. 

3. Get access to hot deals.  Easier said than done, but it’s the typical approach to success, I think.  One way to do this is to have the right professional background.  If you’ve held leadership roles in Google, Facebook, or DoubleClick, it’s more likely that you’ll be able to invest in a buddy of yours who is starting a company. Even if it’s hotly contested, your friend may give you an allocation, or you can make the case that you have something unique to offer because of your experience.  Another approach is to do series B or C deals and pay up for great entrepreneurs.  This is a viable strategy as well, and funny enough, was the advice I got when I started in the venture business (advice that I ignored because it didn’t seem very fun). Another is to closely track an up-and-coming VC or angel investor and find a way to be their go-to investing partner.  In each of these cases, it’s easier to get these deals through a partnership because there’s nothing like a competitive deal to get people’s juices flowing. 

All of these strategies (and others not mentioned) work - since new hot VC’s do emerge and do just fine.  But I do wonder if some potential great talent gets lost because of the dynamics I described in the beginning of this post. 

There has been some chatter on Twitter about the value of pitching to VC associates. Thought I’d lob in my 2 cents on the shuttle to NYC. Full disclosure - I am a senior associate at Spark Capital.

1. Roles have blurred between associates, principals, EIR’s, and VP’s. Regardless of title, different roles have different levels of influence within a partnership. Over the years, I think we’ve seen some title inflation at some firms. It comes down to whether a person can lead an investment. In some firms, senior associates can do this in certain cases (I am able to lead seed investments at Spark). Charlie O’Donnel is an EIR at First Round (and a pretty young guy), but just led their most recent investment in Backupify. But in many cases, associates can’t lead investments, and even principles or young partners will get unusually high scrutiny through the deal process.

2. High quality intros to GP’s > talking to associates > low quality intros. I generally agree with Keith Rabois that you want to get to a decision-maker. It’s common sense, even if it hurts. If I were an entrepreur, I’d try to talk to GP’s I know personally or can get a high quality intro into. But the emphasis is on high quality. A low quality intro is sometimes not much better than a cold call. Also, if you don’t have a quality connection to a firm, getting an associate excited about your company works. An associate pushing for a deal is almost as good as a high quality intro. If not, that VC firm is wasting it’s $ paying that associate. There are many examples of great companies that met their VC’s through associates.

3. Careers are long and Venture is a young person’s game. In many cases, the associates of today are the GP’s or corp Dev execs of tomorrow. It doesn’t hurt to meet them early in their career as you never know where things will go. There are many good GP’s and angel Investors that were former associates: David Cowen and Alex Ferrara at Bessemer, many of the Battery GP’s, Alex Finkelstein at Spark, Chris Dixon, Jeff Fagnan, Larry Cheng, etc (sorry for the east coast bias, but this is off the top of my head). I wouldn’t burn a lot of time with fruitless meetings, but I’d certainly be respectful and get to know the guys I like. Some of these folks will be decision-makers soon enough.

So, those are my thoughts on whether to talk to Associates. Here are two tips if you are talking to them.

1. Be mindful of associates at transition points. Usually, these guys have been associates for at least 1 year, more likely 2. They are either rising stars that will be tested by leading a few investments or guys just trying to survive. If they are the former, they can be great assets. These associates will hussle harder than other VC’s to prove themselves and usually have champions within the VC firm who will give them a lot of support. The latter are dangerous because you might spend a lot of cycles with them and get nowhere. Even worse, they may advocate for a decision, get you funded, but leave the firm in 6 months. Be mindful of the risk of becoming an orphan and make sure you establish a strong relationship with the partner on the deal early.

2. Favor associates with clear domain expertise or a strong thesis. This can be based on their operating experience, blog, or just clear evidence that they know what they are talking about. Meeting these associates can at least be helpful, and typically have a higher liklihood of culminating in serious consideration by partners. It also helps you figure out which firms “get it” in your sector or do not. Typically, I’d be more wary of associates that are clearly chasing momentum. These meetings are less likely to be valuable and could also mean that you are part of competitive due diligence for another deal.

Sorry for typos, this was written on my iPhone.

Larry Cheng at Volition Capital has put together some excellent lists of top VC bloggers and top VC websites by traffic.

Obviously, these measurement methods aren’t perfect (he uses a rolling 3 month average of unique visitors from Compete), but they are directionally correct.  What I found interesting is the correlation (or lack of correlation) between website traffic and aggregate blog traffic from all firm bloggers.  I took Larry’s two more recent lists and did this comparison.  The results are below ordered by website traffic:

Fund Name – (Website Traffic / Total Blog Traffic)

1. First Round Capital – (31,632 / 28,039)

2. Sequoia Capital – (22,441 / 0)

3. Bessemer Venture Partners – (14,825 / 8,262)

4. Highland Capital Partners – (12,704 / 0)

5. Garage Technology Ventures  - (12,375 / 82,838)

6. Draper Fisher Jurvetson – (11,823 / 12,010)

7. New Enterprise Associates – (11,762 / 0)

8. Kleiner Perkins Caufield Byers – (10,924 / 0)

9. Polaris Venture Partners  - (10,217 / 16,991)

10. Benchmark Capital – (10,162 / 23,084)

11. Battery Ventures  - (10,034 / 1,744)

12. Founders Fund  - (9,654 / 21,462)

13. Accel Partners  - (9,604 / 0)

14. Greylock Partners  - (9,445 , 0)

15. Centennial Ventures – (9,224 / 0)

16. General Catalyst Partners  - (9,086 / 0)

17. Summit Partners - (8,270 / 0)

18. Norwest Venture Partners - (8,198 / 0)

19. Founder Collective - (8,189 / 42,937)

20. Spark Capital – (7,834 / 15,487)

21. Foundry Group – (7,787 / 71,547)

22. Technology Crossover Ventures  - (7,503 / 0)

23. Matrix Partners  - (7,309 / 0)

24. Lightspeed Venture Partners  - (6,475 / 15,199)

25. Union Square Ventures  - (6,333 / 132,936)

Some interesting observations:

1. There are a lot of zeros.  It was surprising to me to see how many top firms don’t appear to be blogging at any scale.  Again, Compete may fail to report the traffic of some of these folks, but that probably means that scale is minimal. That said, most of the excellent firms like Sequoia, Accel, Kleiner, etc have good reach with their websites regardless of whether or not their partners blog.  I also know that at least one zero will go away with the next version of the list since David Skok started what looks like will be an excellent blog.

2. Blogging puts firms on the radar.  It’s interesting to see some relatively new firms come on the scene in recent years and build very broad awareness.  For better or worse, brands do matter somewhat in venture, and it’s always a tricky thing for a new fund to figure out how to create awareness. I think expressing your thinking openly and engaging the tech community in a dialog is a great way to do that.  It’s impressive to see Founders Fund and Founder Collective gain mind share very quickly.  And part of it has to do with one or two very vocal individuals who put their thoughts out there.  As a side note, for those of you who do not read Chris Dixon’s blog or  Dave Mcclure’s blog you are totally missing out.

3. Social media creates unprecedented reach.  Event the best known firms only get 10-30K hits on their website.  It should be no mystery why that is - the content is rarely refreshed, and it serves mostly as information and marketing pages to entrepreneurs who are researching a particular firm.  But blogging (and social media in general) expands the voice of VC’s way beyond a bio and list of companies. It’s content that’s actually helpful and appeals to a much broader audience.  Union Square Ventures for example has over 100K uniques, 20x the uniques on their website.  And the richness of their content justifies it (for example, see Fred Wilson’s new series on MBA Mondays).

This last point makes me think more broadly about the reach of VC’s on the internet.  Stay tuned as I pull some additional data together.

I’ve been thinking about this post for a while.  Basically since the great NYT Piece came out on Shane Battier. I think Shane’s story is a remarkable one, and there are a lot of lessons that can be applied to startups and to careers in general.  It’s also interesting to juxtapose his experience with a lesser known Blue Devil - Chris Burgess.

Shane Battier and Chris Burgess were both in my class at Duke.  Both were very highly touted new recruits on an amazing freshman class that also included Elton Brand. Both were McDonald’s High School All Americans.  But they had very different careers in college:

Battier: (Year: PPG/RPG)

1998: 7.6/6.4, 1999: 9.1/4.9, 2000: 17.4/5.6, 2001: 19.9/7.3, 2002: NBA

Burgess: (Year: PPG/RPG)

1998: 4.3/3.4, 1999: 5.4/3.9, 2000: Transferred, 2001: 7.8/5.9, 2002: 13.2/7.2

Today, Shane is with the Houston Rockets and one of the most well regarded role players in the NBA.  Chris has bounced around the European league and is currently playing with a team in Dubai.

I think there are a couple generalizable lessons from these two careers.

1. Find product/market fit early, and be realistic when it isn’t there.

In this case, the player is the product and the team and the NCAA broadly is the market.  Unfortunately Burgess didn’t fit into the Duke system.  It was painfully obvious fairly early on.  Coach K typically has one dominant big man, and a bunch of wing players who shoot threes.  Brand emerged early as that dominant center, and Burgess was left without a role.  Unfortunately, he had to battle through it for two years before he transferred, and unfortunately, he also battled a string of injuries once he started playing for Utah.

Startup entrepreneurs search for product market fit from the very beginning.  I think the challenge in the early stages of a company is to find that fit as quickly and as painlessly as possible.  Until you get there, you want to avoid spending a lot of money on a team, marketing, or infrastructure.  The problem comes when a founder is too attached to his product concept, that he keeps plowing forward even when users are only lukewarm about the product.

Sean Ellis has a very simple way to measure whether PMF is achieved.  The basic idea is to get to a point where 40% of users say they would be very dissappointed if they could no longer use your product.  I think this is something all early stage companies should be measuring and trying to achieve.

In Burgess’ case, he did not achieve PM fit at Duke.  Unlike a web startup, basketball players can’t experiment anywhere near as nimbly with their product. So he had to make the painful decision to leave after two years, redshirt for one year, before continuing his career in Utah.

2. Do A Few Things So Well It Becomes a Thing of Beauty

Shane Battier fit well within the Duke system.  He was very versatile and was a great defender and rebounder.  But he started at Duke as an all-around smart player.  I think it was pretty clear early on that he wouldn’t be a dominant superstar.

What Shane did do was focus on a few things that he did very well, and perfected them.  Specifically, he became the best defender in the NCAA.  He also made an art out of taking charges (a stat that most people don’t pay any attention to). When players faced Shane 1-on-1 when driving the basket, you could actually see fear in their eyes as he got into position to take a charge.

It’s also interesting to see what Shane didn’t become.  He didn’t handle the ball very much, and actually looked quite awkward doing so.  His rebounding numbers didn’t go through the roof, and he didn’t really create scoring opportunities for himself.

A lot of startups have big aspirations of how the product will evolve.  Entrepreneurs are excited about solving huge problems and there are a lot of them out there to tackle.  But most game changing companies start out doing one thing extremely well.  In fact, they do that one thing so well that they uncover unique opportunities that weren’t obvious before.  As an early stage company, it’s important to figure out what it is you will do far better than anyone else.  The most dangerous startups are probably the one that do everything ok, because it’s not immediately obvious that things aren’t going to work out.

3. Know Where You Hope to Get To and What You Need to Get There

Great startups can’t be single product companies that do only one thing well forever.  They eventually have to mature and become real, meaningful businesses. In the same way, great college basketball players often struggle to make the leap into the NBA because their areas of strength are insufficient in a much more competitive league.

I don’t know how intentional this was, but Battier seemed to have a plan for what an NBA version of him would look like, and evolved him game to fit that vision.  During his junior year, he added a three point shot that made him a viable offensive threat.  In the NBA, he improved his quickness and evolved his defensive abilities to be able to handle quicker guards and forwards as opposed to the post players he had defended during most of his college career. His evolution was amazing to watch.  It seemed almost perfectly calculated, fit his god given talents, and matched the needs of the NBA perfectly.

Often, I meet with entrepreneurs who don’t have a great core product that I think could achieve PMF.  But even the ones that do need to have a clear idea of where they are going and the steps necessary to achieve those goals.  Things obviously change over time, but it’s comforting for an investor to know that the entrepreneur has a reasonable roadmap to becoming a big successful company.  Good entrepreneurs know this is more than just imprecise jargon.  It usually involves deep appreciation for the market they compete in, intimate understanding of competitors, and knowledge of the 2 or 3 things that need to go right for their company to win big.

Shane and Chris are both pretty young guys so it’s still early in their careers.  I was a huge Burgess fan, and do hope that he can make it into the NBA one day and have a few solid seasons.  For Battier, it will be interesting to see if he is able to squeeze out even more output from his talents and become a real All-Star.  I wouldn’t bet against him - he’s done a phenomenal job so far.

Fall is upon us (although it feels like winter) and for Boston, that means a new wave of folks who are arriving here for studies or new career opportunities.

When I moved to Boston from Silicon Valley in 2005, I had a pretty sparse network of friends in the tech and entrepreneurship scene.   I also found the tech community here a little disorganized and opaque, although I think that has been changing quite a bit in recent years.

Four years later, I think I have a much better idea of what’s going on, and I’m excited about it.  But it took a while to figure out.  So I thought I’d post a little to-do list for folks who want to get integrated into the local tech community and benefit from all it has to offer.

1. Follow this list of entrepreneurs, VC’s, and academics

• David Cancel (blog , @Dcancel)
• Dharmesh Shah (blog, @dharmesh)
• Brian Shin (blog, @brianshin)
• Don Dodge (blog, @dondodge)
• Nabeel Hyatt (blog, @nabeel)
• Furqan Nazeeri (blog, @altgate)
• Andy Payne (blog, @payne92)
• Bijan Sabet (blog, @bijan)
• Jeff Bussgang (blog, @bussgang)
• Lee Hower (blog, @leehower)
• Larry Cheng (blog, @larryvc)
• Tom Eisenmann (@teisenmann)
• Andrew Mcafee (blog, @amcafee)
• Me :) (blog, @robgo)

2. Follow a few journalists and news aggregators

• Scott Kirsner
• XConomy
• VentureFizz
• MarksGuide

3. Go to the follow meetups at least once

• WebInno
• Mobile Monday
• OpenCoffee Meetup
• Dart Boston

4. Hang out where you are likely to have chance encounters (ok, this isn’t really that practical, but it’s interesting to know where VC’s and entrepreneurs tend to go)

• Deisel Cafe in Davis Square
• Andala Cafe in Central Square
• Paramount Restaurant in Beacon Hill
• Henrietta’s Table in Harvard Square
• Naked Fish in Waltham
• The Marriott in Newton
• The Westin in Waltham
• Preschool OpenHouses in Wellesley, Weston, Cambridge, Lexington,  BeaconHill, etc.  (I’m obviously joking here, but this just happened to me, so I couldn’t resist.  We went to an open house at the Cambridge Ellis School, and among the group of parents, I saw 2 VC’s, an entrepreneur friend, and an HBS professor before deciding the school was way out of my price range)

5. Try to meet folks affiliated with the following organizations and companies (the reasoning being that people at interesting companies and organizations tend to congregate)

• PopSignal
• HubSpot
• Betahouse
• DogPatchLabs
• TechStars Boston
• Cambridge Innovation Center

Hopefully this is a helpful start.  Should take a few months to work through all of these.  I know I’m missing a few (I think I’m obviously missing out events and people affiliated with MIT, among others).  Feel free to add additional thoughts in a comment.