All posts tagged with Boston

Act II: Golazo

For the last couple years, when people have asked me what is needed to improve the startup eco-system in New England, my response has been “more shots on goal”.

I have firmly believed in this.  It was (and continues to be) important to break the impression that starting a company is only for the extremely experienced and extremely well pedigreed.  I think talented people should be encouraged to take a swing and build something, and more experienced members of the startup community should do more to contribute to the ecosystem.

But I think things have changed a bit in the past few years – activity levels are on the rise, investors are more open to backing younger entrepreneurs, and there are many great projects in the works.  Even while this weekend’s Globe article lamented certain weaknesses in this region, the article points to the fact that the local startup culture is indeed changing.  But as I was quoted in the article, I think this momentum should bring an evolution in focus.  It’s time for the start of Act II, and this act is less about more “shots on goal” and more about “Golazo”.  

For those of you unfamiliar with the phrase, “Golazo” is a Spanish soccer slang for an “awesomely amazing goal”.  In this context, what I mean is that while volume of activity is great, what we need is more truly remarkable, enduring successes that will inspire hundreds more because of them.

Easier said than done, obviously, and I’m still trying to figure out exactly what I think this means practically.  But I’ll offer a couple more specific thoughts.

First, for entrepreneurs, “Golazo” means grander ambitions and building a foundation for enduring companies.  That starts with the strength of early teams.  In recent years, the increased availability of seed capital has led to an interesting tradeoff for talented folks.  Do I join the early team of a startup for a point or two of equity?  Or do I start my own thing and own all of it?  Increasingly, the biggest competitor to recruiting isn’t Google or Facebook, it’s the option of striking out on one’s own (this is actually most acute in Silicon Valley).

I think this is generally a good sentiment.  But I also think that some projects are just more worthy of the efforts of extremely bright people than others.  Plus, being a small part of a monstrous endeavor can be more fulfilling (and financially rewarding perhaps) than being a large part of something less ambitious.  I think (and hope) that we are going to start seeing more teams with deeper density of talent going after more ambitious projects in the next several years.  That’s one of the reasons why I’m so excited to be involved with the founders of Boundless Learning, each of whom could have probably raised money for three different companies, but chose to work together on one massive opportunity.

Second, as a contributor and participant in the startup ecosystem, “Golazo” means investing more time in fewer high-quality areas.  Given the wealth of activity that has sprung up in the past several years, I find that many of the generous mentors and experienced entrepreneurs in our community are spread pretty thin.  We are all trying to be as supportive as we can be, so we volunteer to speak on a panel here, be a mentor there, etc.  But shallow involvement in many projects probably isn’t nearly as impactful as really taking emotional ownership of a company or a cause and being a champion for it.   

I was very impacted by TechStars Demo Day in New York this year when each company was introduced by their primary mentor.  Although I’m sure each team benefited by exposure to many great folks, the fact that one person took it upon themselves to really try to impact one team to be as successful as possible was very powerful.  I hope TechStars Boston is taking the same tact. I’m going to try to bring that mindset with me in some of the things I’m involved with as well.   

I’m excited to see how Act II unfolds. It’s early, but we are building off a strong base with a ton of momentum.  I’m glad to be a small part of it. 

Sad Observations from a Boston Angel Dinner

I was at a dinner last night with folks from local angel groups and other seed stage investors in Boston.

There were a few jokes about how “this isn’t Angelgate”.  But honestly, no one would ever mistake it for that - the conversation was far too lame. 

To be clear, there were some people at the dinner that I really like and respect. And there was a good discussion about innovating on the financing model for certain types of companies, which I think is a great insight by John Landry. 

But here’s the really SAD thing about this discussion.  Much of the conversation was so DEFENSIVE - e.g.:

“How do we protect ourselves from getting crammed down by VC’s?”

“How do we make money when the potential for blockbuster outcomes are low?”

“How do we invest when it’s so frothy?” (funny enough, it seemed like everyone was more conservative recently, so I don’t know where this so-called frothiness is coming from).

All real concerns - don’t get me wrong.  But here was the disappointing thing: No one was talking about how to fight like hell to get into more of the blockbuster deals that will really matter.  No one was comparing notes on how to build a stronger entrepreneneurial ecosystem or how to be creative about helping their portfolio companies succeed. 

Instead, a lot of time was spent belaboring the point that venture capital is so challenging as an asset class.  The mean return of venture was quoted several times.

Guess what, I don’t care.  We are not an index fund, and our goal is not to be average.  I want to spend time figuring out a way to invest in and help build a disproportionate % of the extraordinary companies.  Instead, I heard a lot more complaining about how to make more money in non-extraordinairy deals.

I see where other investors are coming from… I really do.  And maybe I’m just too young and naive, but I actually think that as a seed investor, I do have the chance to invest in the transformative businesses of tomorrow.  If I didn’t think that, I would be making a lot more money doing something else with my time. 

Luckily, there are some seed stage investors in Boston that do think this way.  Very few were at the dinner, the rest were not.  But it’s a small handful.  If you want to know who they are, I’m happy to talk offline. 

Organic vs. Manufactured Community

In publishing my Hitchhiker’s Guide to the Boston Tech Community, I had a heavy emphasis on grassroots efforts vs. big top-down events and organizations. 

This is clearly a value judgement on my part.  I’m a big believer in organic communities that are created by and for the end users.  I’m skeptical of top-down initiatives that are led by governments or large companies that fit their PR agendas but don’t really address the needs of end users.  

Let’s take events and meetups for example.  One of my favorite meetups is PopSignal. It’s an organic event - the founders were both entrepreneurs that wanted a venue to collaborate with their peers.  They keep the meetup pretty small and invitees are asked to bring +1’s to the events to keep bringing fresh blood into the group.  It’s a small network, but a very very high-quality one, and one that has strong camaraderie.  My relationships at PopSignal have probably resulted 10 real business engagements, dozens of productive business conversations, and some real friendships that I know will endure.

Contrast this to some of the entrepreneur events hosted by VC’s.  There is nothing wrong with these - I’ve was involved in planning a few at my prior firms.  I will definitely do so again.  But they are not organic events.  Usually, other investors are not invited, the guest list is generated by the organizing firm, and the community itself does not endure beyond one night of drinking.  Not including other investors is a decision that benefits the organizer (in the short term), but does not benefit the end users (the entrepreneurs).  It’s one of the reasons organic communities end up being better than manufactured ones.  Imagine if Charlie O’Donnel was a tyrant and didn’t allow other investors to join NextNY events!  That would be horrible… luckily, I think that community is strong enough that he would be overthrown if that ever happened :)

A new example of really amazing organic community is being formed at the Harvard Business School.  It’s the startup tribe (www.startuptribe.com).  Professor Tom Eisenmann deserves a lot of credit for promoting this community over the years, but he’ll be the first to admit that all he did was add a little fuel to the potential energy that already existed among the student community.  Every year, there are individuals within the student community that just emerge as the nexus of entrepreneurial thought and activity.  Guys like David Vivero (‘08), Sunil Nagaraj (‘09), and Rafael Corrales (‘10).  Their group of friends and similar startup conspirators informally embodied the “startup tribe”, although you wouldn’t have any idea it was happening from the outside.  Recently, a few really motivated students have tried to create some structure around this by having regular meetups, an online nexus for the community, and other events.  Now, HBS has had a TechMedia Club and an Entrepreneurship Club for years and years.  But I think this Startup Tribe is completely different and the more authentic entrepreneurs will gravitate naturally to this organic community vs. more manufactured ones. 

It’s with this lens that I sometimes challenge what I feel are top-down, manufactured efforts at building community.  I always ask, “why reinvent the wheel and create a new venue for x,y, or z when there is a perfectly fine place that entrepreneurs are already doing their thing?”  I urge folks to think less like city planners and to listen to the community and respond to their needs.  I think Gus Weber at Microsoft does an amazing job at this.  He makes the NERD space available to so many organizations, and it’s easy to tell that he’s not thinking about a direct ROI to Microsoft when he does this.

Fostering a strong culture of innovation is so important.  It builds upon itself and fuels so many good things. But culture and community are really really hard to manufacture.  So don’t.  See what is already happening organically and build from there.  

The Hitchhiker’s Guide to the Boston Tech Community 2011

Boston is a great place to start and build a company.  There is a wealth of resources that are unique to this town and a vibrant community of hackers, business people, and investors at various stages in their career.

It occurred to me however that Boston is a transient town.  Especially for the student population that refreshes a large population each year.  So I’ve decided to create an annual guidebook (more like a 1-pager) to the Boston Startup Community. A year ago, I wrote a “To-Do List for New Entrepreneurs Arriving in Boston”.  So I guess this makes this the second installment of what will now be the annual:

HITCHHIKER’S GUIDE TO THE BOSTON TECH SCENE 2011


This is obviously released before 2011 in order to allow folks who are planning to arrive in Boston to get a head start.  If you have comments of suggestions, please include them below.  I’ll be handing out hard copies of this at various venues in Jan/Feb 2011.  So without further delay:

Large Tech Meetups:

  • Web Innovators Group: Quarterly Demo-Style meetup in Cambridge draws over 1000 members of the startup community each time.  The Grand-daddy. Alumni have been funded by Sequoia, First Round Capital, Accel, Trinity Ventures, and others. 
  • Mobile Mondays: Boston chapter of the world’s largest Mobile professional community. 
  • Founder Dialogues: Eric Paley plays talk show host on this recurring fireside chat style event with Boston area founders. 

Online Resources and Newsletters:

  • Greenhorn Connect: Excellent hub of BOS tech events and resources. Currently, this seems to be the most popular and most comprehensive event calendar.
  • DartBoston: A vibrant community of young entrepreneurs.  Join their online community and attend their excellent events. 
  • VentureFizz: Good newsletter with funding announcements, best local blog posts, and other local tech happenings.
  • Bostinnovation: Great coverage of local startup happenings with a growing network of local writers. 
  • OnStartups: One of the largest online startup communities founded by HubSpot founder Dharmesh Shah. 
  • Founder Institute: Boston franchise of Adeo Ressi’s startup program
  • Compstudy: Kelly Blue Book of Startup Compensation

University Resources

Smaller and High Quality Meetups

  • PopSignal - My favorite regular tech gathering.  Invite only. 
  • Hackers and Founders - New, but promising meetup.  More hacker focused. 
  • Capitalize - Regular pitch events where early stage companies get direct feedback from local VC’s. 
  • Open Coffee - Weekly meetup started by Bijan Sabet and Nabeel Hyatt.  No agenda, just come by and talk tech.  

Coworking Spaces

  • Dog Patch Labs - Free workspace run by Polaris Ventures.  No cost, not formal strings attached. 
  • CIC - High quality, flexible office space.  Higher cost, but great facility
  • WorkBar Boston - Flexible co-working space near South Station. 
  • MassChallenge - Startup competition and accelerator.  Beautiful space in the South Boston Innovation District.

Entrepreneurial Development Firms

Places to Hang

  • Crema Cafe - Great coffee in Harvard Square.  Favorite spot for Eric Paley, Antonio Rodriguez, and Rich Miner
  • Andala Cafe  - Central Square hangout.  Free wifi.  Home of Open Coffee Cambridge
  • Henrietta’s Table - In the Charles Hotel.  General Catalyst is right upstairs. 
  • Paramount - Favorite breakfast spot for the Beacon Hill crowd.
  • VentureCafe - Networking venue within the CIC
  • Voltage - New coffee shop in Kendall.  Jim Koch (Boston Beer Company) is an investor.  My new favorite.

Journalists and News

  • Scott Kirsner - Tech journalist of the Boston Globe.  See his innovation economy blog and follow him on Twitter
  • Dan Primack - Formerly of PE Hub, recently poached by Fortune.  Not Boston focused, but definitely follow his reports of PE and VC financings and the state of the venture market. Newsletter here.  @danprimack
  • Gregory Huang - Xconomy
  • Galen Moore - Mass High Tech

Scaling Companies To Watch (ie: probably hiring)

  • Gemvara - Online retailer for customized jewelry.  Founded by recent Babson Alum
  • CSN Stores - $350M + revenue, 300 employees, $0 venture funding.  Amazing company, and one of the biggest private online retailers. 
  • SCVNGR - Location based challenges.  Backed by Highland and Google.
  • HubSpot - Inbound marketing pioneer.  The current talent magnet of Boston tech companies. 
  • Dataxu - Demand Side Platform for Real Time Ad Buying.  Led by serial entrepreneur Mike Baker
  • Tech Stars - Ok, not a company, but an excellent, mentorship driven seed program that gives rise of multiple companies every year that go on to great things.  

20 To Follow (Being edited on the fly, so not exactly 20 anymore)

Investors:

Entrepreneurs and Thought Leaders:

This is just a starting point.  Enjoy the journey!

A Tale of More Than Two Cities

The latest funding data from CB Insight came out recently.  Om Malik commented on it here.  Fred Wilson did the same and commented on the vibrancy of the NY internet eco-system. 

The data is really great - innovation is alive and well in New York, and that’s why I spend a bunch of time there and have made a number of investments there.  I’m glad that the region has gotten the attention it deserves.

But as I dug into the numbers, I realize that it’s actually more than a tale of two cities.  The message it paints about my hometown of Boston is pretty darn strong. And to be honest, I think that Boston gets far less attention than it deserves.   

There isn’t as much of a hype echo-chamber around here, but let’s look at the data:

  • Slide 5: MA is still by far the second largest state in terms of receiving VC funding.  The second largest by a large margin.
  • Slide 40: The internet sector is alive and well in MA.  In the most recent quarter, we saw $98M invested in the internet space in 25 companies.  Compare that to $131M in 36 deals in SF, $126M in 31 deals in NY.  Not terribly different given that things can change quite a bit from quarter to quarter.  
  • Slide 40: In Fred’s post, he discusses the capital efficiency of these companies relative to the same data for Palo Alto.  He writes: “The average internet deal in SF and NYC is $3M - $4M.  In the Valley, it was over $8M”.  MA’s average? $3.9M.  Lower than NYC.  So capital efficiency is alive and well here too. 
  • Slide 14:  This is interesting.  What you see over time is that the share of internet deals outside of CA, NY, and MA is INCREASING!.  It seems like internet companies can increasingly be built elsewhere.  It makes some sense actually given the trends of capital efficiency, our excellent communications infrastructure, and the rapid flow of information on the web. What’s that? You say that no “BIG” companies are built outside of the main hubs?  Ahem.  The biggest internet company of the last 3 years is being built in Chicago (Groupon).  Don’t forget that that company probably has more monthly EBITDA than some of the “hottest” internet companies have annual revenue. 
  • Slide 14: BTW, note that MA has actually slightly increased share in terms of dollars in the internet, while CA and NYC have slightly lost share.  I don’t read too much into this because you don’t want to draw too much from quarterly data.  But it’s interesting nonetheless. 

I’m excited about this region, and the data is promising.  There are certain centers of excellence here that are really exciting - even though they don’t get as much play.  For example, take mobile advertising (a pretty hot sector).  Of the 4 $100M+ exits in this space, 3 have been in Boston (Quattro, Enpocket, and Third Screen).  We also have some awesome companies in many other exciting sectors like ecommerce (CSN Stores, RueLaLa), travel (Tripadvisor and Kayak), SAAS (HubSpot, Constant Contact, etc), Cloud (Carbonite), the list goes on. 

It’s an exciting time to be an investor in internet enabled businesses.  You have never before been able to accomplish so much with so little.  I’m thrilled to see the fervor around the NY market.  I’m also thrilled to see such strong data in the BOS region, and the thought that we’ll see more exciting companies built anywhere there are smart, driven people with the will to solve meaningful problems.  It’s an exciting time. It’s the best of times. 

An Entrepreneurial Renaissance in Boston

Yes!  I’m saying it - we are in the early days of an entrepreneurial renaissance in Boston.  Even in the wake of TechCrunch Disrupt.  Even though every VC that talks about the greatness of New England is doing so from the Acela to NYC. 

Those of us who have been engaged in the Boston startup eco-system know that this is the most excitement we’ve seen in many years.  I was having lunch with a prominent local entrepreneur, and he remarked that there is more startup activity among young entrepreneurs in Boston than anytime in the past 10 years.  And as I’ve said before, more shots on goal will result in more big winners.

There are many reasons for this.  I’m going to talk about two.

1. We are seeing multi-generational involvement and mentorship in the Startup Community.  This is thanks both to successful entrepreneurs who are actively giving back, as well as motivated young entrepreneurs who are creating buzz and density among their peers.  For the late 20’s - early 30’s crowd, there is the PopSignal group led by Brian Balfour and Jay Meattle.  It’s THE entrepreneur gathering for the up-and-coming founders, but you will almost always see some of the more successful local entrepreneurs attending to give back to the community (guys like David Cancel, Andy Payne, Rich Miner, Mike Baker, and others). And the early 20’s crowd is not being undone, with Dart Boston getting under-30 founders together to collaborate and get feedback from top VC’s in town.  

2. There is critical mass of great companies (and recent exits) where future founders and entrepreneurial executives are being trained. Not everyone will found a company right away.  For those that don’t, it’s important to have pockets of excellence where talented folks can work, learn a trade, and gain experience behind successful entrepreneurs.  It’s also nice to put a little money in one’s pockets too, to create flexibility to experiment.  Boston has several very important pockets of excellence and great companies that are talent magents.  Including:

I think what’s happening in NYC is great, and I definitely spend my fair share of time there and in Silicon Valley (and have angel investments in both locations).  But I’m thrilled to live in Boston, and I’m partially glad that other investors are spending time elsewhere.  Leaves more opportunity for me :)

If You Are a 20-Something Entrepreneur in Boston, Check This Out

I previously wrote a To-Do list for new entrepreneurs arriving in Boston.  It included a bunch of folks to follow on twitter and on their blogs, events to go to, and companies to get familiar with.

I’d like to add a new to-do on the list, especially if you are a younger entrepreneur.  Check out Dart Boston - a community of entrepreneurs 30 and under helping one another start their businesses.  These guys have sprung up out of nowhere in recent months, and I’ve been really impressed by their level of activity and creativity.  For example:

Pokin’ Holes: A weekly meetup and video show where one local entrepreneur presents their company and gets grilled by their peers.  The show moves around Boston in an effort to engage the entrepreneur community in different areas.  Tonight’s event is at Tufts.

Capitalize: A monthly show where one company pitches to a VC or angel investor.  You get to see the pitch and feedback streamed live.  This month, it was at Kepha Partners with Eric Hjerpe.  In May, I’ll be on the show at Spark Capital.

Rule 53: A podcast that features a series of interviews about startup life, business, and tech.

I don’t know how these guys and gals have time for all this, but I’ve been very impressed and think it’s an excellent addition to the local tech scene.

Where to find angel funding in Boston

I’ve often heard that there is a shortage of seed-stage investment capital in the Boston area, especially in the consumer realm.  Nabeel Hyatt, founder of Conduit Labs put it pretty succinctly:

“This is in IMHO *the* biggest impediment to a stronger startup culture. There is no ecosystem of consumer angels in Boston, at all.”

There are quite a few large venture firms in our region, but not as many who will a) write a bunch of $50K-$250K checks to help a very early stage company get going or b) can invest in deals that might not have venture scale potential but is still a sound business.  Some venture capital firms are active in this sector, but for a number of reasons, can’t fill the void completely.

I was trying to do some research on this market, and found that it’s actually pretty hard to figure out who could provide angel funding in this town.  So here is a list of the folks that I know are active at this stage (with a bias for my sector of focus).

Professional Seed Investors

These are folks who’s primary goal as a business is to fund seed-stage companies.  This does not include large VC firms (ie: any fund with $’s / investing partner > $30M).

It seems that there is clearly a dearth of players in this sector.  The groups above have wildly divergent strategies and typical check sizes.  I think the more groups like this that are successful in the Boston ecosystem, the better.

Angel Networks

These are networks of high net worth individuals that pool their resources and deal flow.  There are often coordinators for the networks, or set events when these angels come together to evaluate opportunities.  A lot of folks have discussed the pro’s and con’s of these networks, so I won’t get into that here.  Xconomy has a nice summary of these groups here.  I’ve heard that quite a few of the members of these angel groups also invest individually.

Individual Angels

If I were raising angel money, I’d try to tap value-added individuals first.  It’s a lot of work, but I think getting someone with relevant experience to commit money and time to your new company is very helpful.  As a venture investor, we love investing with value-added individuals. I also find that companies that have these sorts of individuals involved tend to make better progress before raising an institutional round.  This is an incomplete list, so please add more folks in the comments.  If anyone here would rather not be on this list, please feel free to email me directly at rob at sparkcapital dot com and I will remove you.

  • Bill Sahlman - well known HBS professor and angel investor.  I don’t think his list of investments is typically published, so I won’t disclose them. But anyone who has taken his class knows that he has invested with Jeff Parker for years.
  • Shikhar Ghosh and Guli Arshad - former entrepreneurs and executives.  Investors in companies like Skyhook Wireless and BzzAgent.
  • Dave Balter - CEO of BzzAgent.  Investor in a few companies, also an active advisor to quite a few others.  Involved in Perk Street Financial and I believe Runkeeper.
  • Steve Kane - Founder and CEO of 3 successful startups. Investor in companies including Pangea Media and Conduit Labs.
  • Andy Payne - Successful entrepreneur and OpenMarket co-founder.  Investor in companies including fansnap and care.com and Shareaholic.
  • Dharmesh Shah - CTO and Co-founder of HubSpot.  Investor in companies including Visible Measures and OneForty.
  • Brian Shin - CEO of Visible Measures.  Investor in Shareaholic and Hubspot.
  • David Cancel - Founder of Compete.  Investor in Shareaholic and involved in a bunch of other companies like Geezeo, Visible Measures, and FlipKey.
  • Stephen Kaufer - CEO and founder of Tripadvisor. His personal investments are not widely publicized, but I’ve seen a few companies that he has invested in personally and he is listed as an investor at weddingbook.
  • Scott Griffith - I have no idea if he is investing personally, but I know that he has helped companies as an advisor, including runmyerrand which recently received further angel funding.
  • Don Dodge - Fomrer Microsoft executive and serial entrepreneur.  His personal investments aren’t that public, but he is an investor in CitySquares.
  • Ed Roberts - Chair of MIT Entrepreneurship Center.  Investor in Shareaholic and Visible Measures.
  • Bill Warner - Founder of Avid Technologies, investor in Posterous.
  • Jean Hammond - Member of a few angel groups and founder of GoldenSeeds. Investor in JAM Technologies and Zipcar.

Anyone else I’m missing?  Please add them in a comment.  And of course, I’m always in the market to hear about early stage investment opportunities and get to know local angels better.

A “To-Do” List for New Entrepreneurs Arriving in Boston

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

2. Follow a few journalists and news aggregators

3. Go to the follow meetups at least once

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)

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.

Rob Go Thanks for visiting my blog! Learn more about me or ask me a question.