Thinking About Thinking

Today marks the first entry in a new series called “Who Is”.  This series will be about getting to know people in a slightly different light.  My favorite part of the work we do at Volition Capital is getting to know people.  So, I figured I take a little time each month and tell one person’s story.  Some people I profile will be known commodities to the readers of this blog and others might just be folks who have an interesting story.  We’ll see how it goes.  Today’s first entry is about Scott Kirsner.  Scott is a well known journalist in the greater Boston innovation economy, which is appropriately the name of his blog.  Arguably, he has interviewed more people in the Boston-area technology and entrepreneurial communities than anyone else.  So, I thought it’d be fun to turn the tables on him.  Here we go…

LC: The title of this post is going to be “Who is Scott Kirsner”.  So, who are you?

SK: Well, I think I’m a journalist who writes about innovation often in the Boston area but often in other places and other industries.  My main interest is in the Boston and New England ecosystems.  I have written a couple books and help organize a couple conferences like Nantucket and Future Forward.  And, I blog and do video and am interested in all sorts of new media ways of doing journalism. 

Can you give me your 60–second life story?

Grew up in Miami.  Always interested in technology.  I learned how to write Basic at a very young age, fell in love with my Apple IIE computer, and   briefly ran a BBS in the pre-web days.  Always really liked journalism and writing so I thought I’d have a career in that.  I briefly went to a school for the arts and studied saxophone, so I thought maybe I’d have a jazz music career, but then when I came up to Boston to go to BU, I noticed all of these Berklee School of Music kids were much more focused and better on the music front and gave up the idea of playing saxophone professionally.  Came up here to go to college and stuck around ever since, with the exception of 2.5 years that I spent living out in San Francisco to get a taste of the west coast scene. 

So you went to a performing arts high school?

Yes, I went to a performing arts high school.  I studied journalism at BU.  And then after college, I worked in management consulting for a couple of years just because there were no journalism jobs to be had.  I kind of worked at marketing, editorial issues, and started the first website for this management consulting firm.  Built in ground up in the days of Mosaic.  And that led me to my first job at the Globe which was helping to design, build and launch Boston.com in 1995. 

What’s your family background?

I have one son and we live in Cambridge which is a great place to live.  Most of my life happens along the red-line.  I go long stretches without driving which I really like about Cambridge.  I grew up in Miami in the suburbs, in the years before Miami was a really hip place to be.  I go to South Beach now and I don’t have the right clothes, am not in good enough shape, I don’t have the tan.  I’m very out of place there. 

What are your other interests?

I’m playing a little more piano now more than saxophone.  Just trying to improve my piano playing skills which are not very good.  It’s fun to do sing-a-longs with my little son.  It’s better to do sing-a-longs with piano than saxophone.  Other interests – I collect some vintage posters, vintage movie travel posters.  I like to go to drive-in movie theaters in the summer.  There are still a few of those that exist.   

What’s the best one?

The best one people don’t know about is the Mendon Drive-In and it’s actually just out of 495.  Totally awesome.  The best one people do know about is up in Cape Cod in Wellfleet.  The Wellfleet Drive-In. 

So you wrote a book about movies, what’s your favorite movie?

I’m not sure I have a favorite.  My favorite movie would be something cheesy from my childhood in the 80’s like Back To The Future.  It’s from the love of technology and of tinkering and crazy science projects.  It’s not a really good movie.  I also get the chance to go to a lot of film festivals so I see a lot of independent film.  So the latest movie that I saw down at SXSW, there was a documentary about Saturday Night Live called Saturday Night.  I really enjoyed that. 

Tell me about your greatest achievement before your professional career?

I started an underground magazine when I was at BU called The Rumor – a humorous satire magazine.  That was my first experience trying to manage people, manage writers, manage salespeople and doing a start-up.  That and some other start-up business experiences have given me a good sense of just how challenging it is for a lot of the people I write about to get that first dollar of revenue.  As an aside, I actually sold the very first ad on Boston.com because my manager told me we needed some ads before we launched.  Even though I had a mostly editorial job, I went hustling on Newbury Street to all the different stores because it was right around the corner from our office. 

Who bought the first ad?

This second hand clothing store called Second Time Around.  Of course, this was in 1995, selling an ad also meant building a website.  It was not a really profitable endeavor.  “Yeah, we’ll buy an ad on your website, but we don’t have a website to link to so can you help us with that.”

What’s the political or social issue you most care about?

The Start-Up Visa thing is really important.  All of my political issues are linked to entrepreneurship.  I think it’s important to help people who want to start companies here, wherever they’re from.  In the state, getting rid of non-compete agreements would be really positive for the innovation economy here. 

Your pet peeves?

I don’t have a lot of pet peeves about other people.  My personal pet peeve is running late.  That drives me crazy.  One that has been surfacing lately is people who leave you a phone message and say, “Hey, this is Scott Kirsner, I’d love to talk to you, can you call me back at this number?”  And you don’t know what it’s about.  And you’re playing this long game of phone tag.  And they don’t put any information in the phone message.  Whenever you try and email them they just want to schedule a phone call.  I’m done with the we need to have a phone call about everything mode of interaction.  It’s very 20th century.

Your house is burning down, your family is OK, what’s the one item you take with you?

I think my wife would be mad if I didn’t say the cats.  But, if they’re part of the family, to be honest, I have a framed marriage contract.  In Judaism you often have a nicer, decorative marriage contract sign.  We have a really nice one at the bottom of our stairs.  I think that’d be a good thing to take both from my perspective, and my wife’s perspective. 

What’s something you’re wrestling with?

I’m wrestling with what makes a good newspaper column to print on Sunday, and what makes a good blog post.  I think of my blog readers as being a little more insidery and participants in the ecosystem here, and the Sunday column readers as being a general newspaper reader who may not know or care about venture capital or start-ups and trying to find interesting stories for them that don’t feel very insidery. 

Do you have different journalistic standards for both?

Yeah, I’m trying to get things accurate.  The great thing about blog posts is you screw up and you can instantly correct it and strike thru the words where you made a mistake and update it.  In a way, it feels a little bit less damaging when you make a mistake as opposed to having half a million copies of the Boston Globe that you can never correct.

Right now, you’re writing books, your hosting conferences, you’re writing for The Globe, you’re blogging – can you rank order them in terms of your personal enjoyment?

Right now I’m doing a lot of conference organizing, so I’m a little bit overwhelmed by the sheer amount of that.  So, that’s not my highest level of enjoyment right now.  Although ordinarily, I do enjoy that a lot.  And certainly when the conferences roll around, I just enjoy seeing a mix of interesting people talking about fun stuff often without powerpoint in an unstructured way.  For me it’s about being out and about, not so much writing the column, sitting in front of my laptop or writing a blog post.  It’s more about being out and about, hearing what people are working on.  Meeting entrepreneurs at conferences or little get togethers whether it’s OpenCoffee or webinno.  I like being around the entrepreneurial energy.

You’re known as the innovation guy, you’re pushing innovation here.  When did that start, how did you get onto that theme, where did it come from?

I left full-time employment at The Globe in 1997.  I started doing a lot of freelance writing for Wired Magazine, Wired’s website, Fast Company, and a bunch of other places, CIO magazine.  Then in 2000, at the height of the dot com, The Globe asked me to do a weekly column on Internet stuff in Boston because I had helped launch their website and had been doing this freelance writing.  Over time that expanded, as Internet stuff stopped happening as much in 2001, and in 2002, I started expanding to other areas of technology – life sciences, energy, any kind of start-up enterprise.  When I got back from CA in 2007, I just really felt like no one in California talks much about Massachusetts, or knows what’s happening here, and that was a little troubling.  I wanted to take a more of an activist role with the column.  What are the issues that we ought to think about, work on, and talk on that are holding us back, not just in a Boston versus Silicon Valley way, but let’s be a globally competitive place that attracts people to work in all kinds of innovative industries. 

How would you assess how you are doing?

Well, I think there are a lot of people who are more influential at it than I am.  I think Bill Warner, the founder of Avid, is very involved with the Mass Tech Leadership Counsel.  I think what David Beisel has done with webinno has been very powerful for the community.  I don’t think I’ve been a major influencer, but probably in an annoying way, I try and write about things that would move the needle and would make Massachusetts and New England a better place for entrepreneurs and just encouraging people here to be a little louder and prouder about what we do here – be more self-promotional and be more promotional of the region.

How many people do you think you’ve interviewed in your career?

I’m so bad at math.  If you just talk about the Globe column – this is my 10th year of writing the weekly column.  That’s 50 columns per year, and on average I interview 7 people for every column.  So, that’s 350 people a year times 10.  So, let’s say 3,000–3,500 people just for the Globe column.

What’s your most memorable interview for whatever reason?

I’ve had the chance to interview lots of interesting people for books.  One really fun interview is I interviewed Morgan Freeman in a trailer of the set of a movie for one of my books.  It was just a really interesting conversation oddly about movies being delivered over the Internet which he was really an early promoter of.  That would be one that stands out for me.  Another one was interviewing Chad Hurley from YouTube very early in the days of YouTube in 2005.  I was writing a piece for the NY Times.  It was very hard to tell at that time that YouTube was going to be the winner in online video. 

What do you consider your best piece of reporting ever?  And conversely, where did you really screw it up?

I feel like occasionally I have an article that doesn’t turn out the way I hope.  For me, the thing that is really successful is having a central story or anecdote about an interesting people that you can really relate to – like a famous column that I wrote about you once.  So often I do feel like I fall short.  Nothing comes to mind as being egregious like I wish I could take that column back.  I don’t know if I want to judge what the best piece of reporting I’ve ever done.  There are a couple of columns that have illustrated conflicts between entrepreneurs and VCs that I got really good response from – not from the VCs usually, but just the entrepreneurs.  Because I think the power dynamic entrepreneurs in a lot of cases being supplicant and needing the money and needing it from VCs, and the VCs having the ability to look at every company in the space and decide where they’re going to invest. 

What do you think would be the words that a typical Boston-area VC would use to describe you if I asked them, “What do you think of Scott Kirsner”?

“Who?”.  I don’t think everyone knows me.  Maybe they know who I am.  Probably annoying, inaccurate, irrelevant.  I don’t think most VCs feel like I have that much of an impact and they probably think what I’m doing is constantly just needling them for insignificant stuff.  Which is sort of true.  The VC’s main job is to make money for their LPs and everything else is secondary.  That’s the way I look at the bottom line.  It’s not to maximize the return for entrepreneurs or team members or do great things for the community.  When I’m needling them about doing more stuff for the community, you should be blogging, sharing your thinking and your vision – a lot of them think that’s just annoying and maybe obnoxious too.

For the VCs that do think that, what would you want to say to them?

That my job is to be annoying and needle people and write about the issues that could be holding back the regional economy and could improve it.  You may not agree.  I am interested in hearing from people when they don’t agree.  I love when people tweet their rebuttals or email me or do a blog post about it.  I think everything is a conversation.  The thing that is great about social media, the people that disagree with you and the people I write about, have a big platform now to share their viewpoint.  It’s not just the big media having the only platform and I think that’s a really positive thing. 

What do you think an average Boston-area entrepreneur would say?

“How come you haven’t written about me?”  I hired this expensive PR firm, they’re pitching you all the time, why haven’t you written about me?  My response is I’m just one person.  I try to write about the stuff that feels the most interesting and relevant at the moment.  It’s not my agenda to write about every company.  In a way, I’m a little bit frightened about the TechCrunch approach to journalism, or a lot of blogs, where every company that gets $0.5M in funding is worth writing about even if it’s the 36^th company in the location-based check-in game space.  To me it’s not interesting to write about that 36th company getting funded to take on FourSquare. 

If you could theoretically have stock in the company of any entrepreneur that you’ve interviewed, which company would you want?

That would be a real conflict obviously.  If only in theory, to be honest the company that is most promising right now just because they so own the business model is Zipcar.  They’re not really a pure technology company at all.  I just feel like Robin Chase and her co-founder Antje Danielson were just so brilliant in bringing that business model over from Europe.  They and Scott Griffith have been so great at expanding it.  That just feels like a company is poised to be a nationally or globally relevant and really successful company to me.  It’s changing the way people live in a fundamental way.  The only thing I’d disclose is I’m a Zipcar member so I use it and have that experience of wow, this has stopped us from buying a $15,000 second car that has insurance costs and gas costs and registration costs. 

When you look down the road 10–20 years, where do you hope to be, what do you hope your legacy is, what will you be doing?

I’d like to transition by then to being a snowboard instructor in the winters and take my summers off.  But, in terms of impact, there are a lot of great initiatives that are trying to shape Boston and New England.  I think this is one of the most innovative corners of the world and I want to help spotlight what people are doing here.  The analogy I use a lot, because I grew up in Miami, I think of South Beach.  I grew up in South Beach in the 1980’s – I didn’t grow up in South Beach, I grew up in Miami, but when you would go to South Beach, it was a totally abandoned place.  Two kinds of people lived there – senior citizens and the muggers who preyed on senior citizens.  In 10 years, it totally changed.  All the New Yorkers want to have a second house there and go there on vacation.  You have giant art festivals.  I do think you can really change the culture of a place in a short period of time, and I’m hopeful that’s happening in New England.  I think a good achievement would be to spotlight, write about, and help bring attention to the work that other people are doing to really change the culture of this place.  Change the way that we think about ourselves and change the way the rest of the world thinks about us.