Succeeding Beyond Free

July 13th, 2009

Free place to sleep by Brad StablerMalcolm Gladwell lit a few fires last week with his (broadly perceived as negative) review of Free: The Future of a Radical Price, Chris Anderson’s new book. 

Gladwell is more negative on Anderson’s examples (such as YouTube as successful free offering) and the myopia of what Gladwell calls “technological utopians,”  though, than I think he is on what’s being called “freeconomics” (i.e., business models built around free offerings).

As Gladwell points out, “free is just another price.”  And we’ve seen for many years prices set low to maximize product/service uptake.  The example I tend to cite is Wal*Mart – its management sets food prices so low that the company basically breaks even on it, but by having groceries they change their stores from ones that are visited once every month to stores that are visited once every week.  And when customers purchase groceries, they purchase other goods with higher gross margins.

We’re seeing the same thing happen with consumer facing services on the Internet.  It’s not news that most of the information offerings online are “free.”  Google, Facebook, Twitter, NYTimes, Yahoo!, Mint…the list goes on.  Their managers are maximizing both uptake and retention in a hypercompetitive environment where adoption and switching costs are relatively low.  Having established giant traffic bases with free offerings, they are able to make money in other ways.  Much of it is advertising, but increasingly we’re seeing other avenues where consumers pay for additional services, a model long ago (at least in Internet years!) termed “freemium” – i.e., a free service with paid-for premium options.  Facebook, for example, is expected to do ~$550 million in revenue this year, most of that from advertising, but an estimated $75 million from virtual goods [via].

Fred Wilson writes: “Free gets you to a place where you can ask to get paid.  But if you don’t start with free on the Internet, most companies will never get paid.”  For consumer-facing info services, I think that’s not far off.  There will always be services that can charge consumers from the get-go and succeed doing it – e.g., Reputation Defender, a company that charges $10/month to monitor one’s digital presence, something that school and job applicants in particular REALLY care about.  And there are cases where the cost of service delivery per user is too high to justify a freemium model and/or the service is truly differentiated and free may devalue it (see Freemium did not work for Phanfare).  But even Gladwell ends his piece postulating that Apple might eventually give away its iPhone in order to boost revenue from its app store downloads.

Free is a customer acquisition strategy, and clearly not an end-game.  For consumer services, understanding in detail what works as an adjunct to free (e.g., virtual goods, other forms of e-commerce, premium service offerings for “power users,” and yes, advertising) will set companies apart.  And frankly, it’s a place for new startups to make money.  “Succeeding beyond free” is a pain point, one begging for more turn-key business-to-business services.


As sidebar, game designer Dan Cook recently wrote a lengthy call-to-action to online flash game developers – it’s a huge space (Mochi Media, a single network of online flash games reportedly attracted nearly 100 million users in April) but not being effectively monetized.  In his post, Dan lays out a number of ways to “ask for money” from the user (something most games don’t do), all good examples of adjuncts to free and many of which can translate into social networking or other forms of online publishing [hat tip to Jeremy Liew]:

  • Time gates - Players can play for some period of time and then they are locked out until they pay.  For example, players could play for 45 minutes - 1 hour (effective free trial times in the casual space) and then pay to play longer.
  • Content gates - Players play an initial teaser portion of the game for free and then pay to unlock access to additional content. For example, players could pay to unlock all the levels in a game.  This is how many shareware titles worked.
  • Aesthetic items - Players purchase non-gameplay additions that increase their identity or status.  For example, players could pay to give their character a cool outfit that they can show off to their friends.
  • Abilities - Sell unique abilities that let players experience the game in a new way.  For example, players could purchase new jumping boots that let them fly through levels in a way that lets them re-experience the game all over again. 
  • Bundles - Virtual items can be bundled together to create additional value.  For example, if people love buying food for their virtual pet, let them buy a 10 pack of food for a 30% discount.
  • Consumables - Some abilities can expire after a period of time or after a number of uses.  For example, you could buy a potion that increases your strength, but you can drink from it 3 times.  Also known as “item rentals.”
  • Subscriptions - If certain abilities or bonuses are valuable long term, consider charging a reoccurring fee.   For example, you could offer extra storage for advanced players, but charge a monthly fee.
  • Stackable subscriptions - If certain abilities are additive (such as an experience or currencies multiplier), let players buy multiples of the same thing.
  • Rare items - Limit the number of items available so that players feel special when they purchase them.
  • Time limited items - Offer some items for short periods of time so that players feel that they lucked out finding the product in time.
  • Sale items - Set a standard pricing system for items and then offer some items for sale.  This works great with time limited offers. Again, players love to get deals.
  • Gifts - Players seek to maintain social bonds by gifting other players with items or abilities.
  • Accelerators - Many games have a ‘grind’ that artificially lengthens the game. Players with little time are willing to purchase items that let them reduce or eliminate the time consuming activities in the game.
  • Physical goods - T-shirts and other branded items


Photo credit: Free Place to Sleep, originally uploaded by Brad Stabler

VCDB: One Week and Many, Many Searches Later

August 12th, 2008

Well, it’s been a week since VCDB went live and the response has been overwhelming… and instructional.  First and foremost, I’ve been surprised by the impact that Twitter has had on traffic.  As a group instant messaging app (oversimplification, I know), it’s a powerful one.  A few “tweets” from well-”followed” twitterers set off a chain reaction of visits, not only from Twitter but also from Facebook where thousands of folks have installed the Twitter app to auto-update their Facebook status with their latest tweet. (If your head is spinning from the jargon, head here for a primer.)  The below screenshot from Twitter’s search tool shows a slew of folks “retweeting” an initial chirp from Guy Kawasaki.  In this case one can even see folks targeting the recommendation.  Note that FussyPants (below) has friends who think she’d be interested in a venture database.  Wild.  “Word of mouth” is increasingly transparent.


I also have a few folks to thank for spreading the word more formally.  Guy Kawasaki, in his typically entertaining fashion, cracked me up by covering the launch with a post titled, “Newsflash: Young VC Adds Value.”  The jury’s still out, I think, but thanks, Guy.  Dan Primack at PE Hub (article behind subscriber firewall), Alain Sherter at (article here), and Tim Berry at (article here) - professional journalists - each posted about the tool as well, as did a number of others.  Thanks, folks.

And the numbers?  Some 11,000 searches and 1500+ visits to venture firms’ websites (84% of firms in the database have received traffic from the tool) constitute, to me, fairly robust usage over a single week.  App improvements are warranted and on the way.

Announcing VCDB (Venture Capital Database)

August 4th, 2008

image This one’s been a long time coming, so I’m glad to finally be throwing back the curtain.

In short, I’ve built a tool meant to help open doors in the venture capital financing community.  If you’re in a hurry, give it a go now; otherwise, read on for the details and development story.


So what is VCDB and what does it offer?

Simply put, it’s a search tool focused on the venture capital industry.

Enter a city in the “City” field, and VCDB will return all firms with a matching location.

Plug in your college in the “Bio Keyword” field and VCDB will return all professionals with your college name in their bio, sorted by firm.

I’ve suggested a number of use cases within the tool under “Usage Tips”; here are a few highlights:

  • Entrepreneurs seeking financing - identify potential funding sources
  • VCs - gather a reference call list for an entrepreneur’s prior venture-backed company or find co-investors
  • Limited partners - identify potential investment opportunities
  • Prospective VCs or startup employees - discover VCs with which to talk in order to land a job

Matching firms show on a map, and an accompanying listing directory enables access to firms’ websites, email addresses, locations, and investment parameters (assets under management, minimum investment, and maximum investment) as well as professionals’ bios and blogs.  Only publicly available info (i.e., from the firms’ websites) is included.

The underlying database contains information on 492 venture capital firms with 863 locations (an average of 1.75 locations per firm), and 6,773 professionals.  I started with a list of National Venture Capital Association (NVCA) member firms, cut buyout groups and the like, and added a few folks that were on my radar as legitimate firms that should be included.

The dataset is reasonably comprehensive but not all-encompassing.  If you’re not in the dataset and you’d like to be, please use the feedback/data submission form included in the tool or contact me via the header link.  Ditto if you’re in the dataset and you’d like to be excluded.

Please recognize, too, that the data and tool functionality is imperfect.  A collection effort such as this one is bound to generate errors and while I did what I could to reduce them, some surely fell through the cracks.  Moreover, the data is constantly changing as new firms enter the fray, existing ones exit, and professionals move firms, receive promotions, add board seats, etc.  I’m working on tools to automate and/or facilitate community editing and improve the search process.  Thanks in advance for your patience.  Hopefully, in aggregate, what’s there and accurate more than makes up for such imperfections.


Getting started…

At first, I had a “wouldn’t it be neat” thought around the notion of mapping venture capital firms on a simple Google maps interface.  The universe of domestic venture firms is small enough that this would be a possibility without a ton of legwork.  And I liked the idea of visually representing the concentration of firms in New England and Silicon Valley.  More importantly, entrepreneurs utilizing the map might discover firms with geographic proximity that hadn’t previously crossed their radars.

At the same time, a colleague and I had been musing about the relative concentration of certain schools (e.g., Harvard) amongst venture professionals’ backgrounds, and as I began thinking about data collection for the map project, the thought of cataloging investors’ backgrounds was intriguing.

It was also a little daunting.  The NVCA has about 500 venture capital firm members publicly listed on their site, and I thought that was probably the right list with which to start.  Address information for 500 firms seemed manageable but biographical information on all accompanying professionals would multiply the data collection by at least 10x.  “Wouldn’t it be neat” wasn’t enough to justify that kind of work.

But as I thought about the data I was considering, it struck me that there’s a ton of value in investment professional bios.  Previous workplaces, alma maters, non-profit affiliations, hobbies and more find their way into our personal blurbs.  And these are sources of connection - entrepreneurs to VCs, VCs to other VCs, etc - making for a worthwhile endeavor.  I set off to the races (with some serious help from outsourced labor and friends).


Huge thanks to…

This project required an enormous amount of help from others.  First and foremost, Andriy Bidochko did an outstanding job on the user interface and design.  I highly recommend him and his firm for outsourced web application work, particularly as it relates to map integration.  Glowtouch Technologies did a first cut on data collection and Kristine Holthouser facilitated finalizing it.  I never would have gotten started without Glowtouch’s help, and never would have finished without Kristine.  David Yeiser redesigned my blog and integrated VCDB into it.  He’s truly a Wordpress maverick and a first rate designer irrespective of medium.  Todd Higgerson spurred me forward as the project began and put in a hunk of data legwork himself.  Michael Schnuerle of MetroMapper assisted along the way with various design and functionality issues (including the expand/collapse feature of the search bar) leaving a much improved product.  My colleague Lenny also played a big role in enabling some of the technical architecture and offering his hand at tweaks along the way.  And Carson McDonald and John Stammerman each contributed key elements, Carson in the form of functionality and John by untying some visual knots at the end.  Thanks all!

Advice/thoughts/encouragement from my brother Dan, Ashley Cecil, Vik Chadha, Todd Earwood, Chris Pearson, Rob May, Charlie O’Donnell, and Craig dos Santos were invaluable and helped get v1 to the finish line.

And thanks, too, to Chrysalis Ventures for sponsoring the product’s launch and supporting my efforts.  I have the pleasure of working for a stellar firm.


One last thought

The venture industry is witnessing rapidly accelerating transparency - from numerous blogs such as this one to sites like TheFunded where entrepreneurs rate investors.

It’s my hope that VCDB plays a role in developing an “entrepreneur friendly” ecosystem.  Increasingly, I suspect investors with access to the best young companies will be those that are perceived as being value-additive partners; this tool is my effort at starting that process early.  And, of course, I’d appreciate it if you joined this site’s community or can point out an interesting startup (yours, maybe) that I, and Chrysalis, should check out.

Happy hunting!  Here ’tis.


Photo credit: Circus at the Lensic 2, originally uploaded by Stewf

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Word Play: "Tooth to Tail Ratio"

July 12th, 2008

image In the midst of conversation with an investor/entrepreneur out of Dallas, I mentally stumbled over his musing, “Good tooth to tail ratio.” 

This one was new to me, though the startup world is full of bizarre analogies. 

I’m used to baseball metaphors (e.g., single, double, triple, home-run returns), horse racing (entrepreneur as “jockey”), food (”this one’s all sizzle and no steak” meaning hype without the substance), fights (”saber rattling,” often to indicate noise-making with no intent to actually battle), even fire (”he’s trying to boil the ocean with a Bic lighter” meaning thin resources applied towards a giant goal).

For whatever reason, we tend to focus on the primitive.

And I guess “tooth to tail ratio” is no exception.  As it turns out, the phrase is an old military expression that compares frontline (”tooth”) and support (”tail”) assets.

Historically, we’ve seen a massive drop in tooth to tail ratio within the US military - from 90/10 (Civil War) to 40/60 (World War I) [via, pg 39], to what I suspect is much lower still today (consider the last couple decades’ focus on air operations to win a war), though I’m no military expert. 

I wonder if we’ve seen/are seeing/going to see a similar trend in business.  Seen?  Yes.  For certain types of business, the Internet has enabled an automated sales process that’s been a resource game-changer, altering frontline (i.e., salesforce) needs.  As it relates to retailers, this shift has benefited the consumer, leading in large part to lower prices rather than higher margins.  Interestingly, though, some of the very high margin media businesses we’ve seen emerge of late benefit from historically high gross margins as well as headcount efficiencies, but may spend significantly (relative to other expenses) on salesforce in order to drive advertising. 

Offline, the sales automation gains will take time.  We’re seeing these kinds of gains organization-wide such that sales teams have improved lead mechanisms and back-end support (i.e., fewer salesfolks should deliver similar results) but the element of human interaction often remains critical, especially in a B2B context where consultative sales predominate.

The virtual sales avatar has a ways to go for tooth-to-tail to show less bite.


Photo credit: A perfect set of teeth, originally uploaded by Everything is Permuted 

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Market Sizing Benchmarks and Surprises

July 2nd, 2008

image Market makes for a healthy obsession.  Marc Andreesen calls it “the most important factor in a startup’s success or failure.

And there are plenty of market intricacies to ponder but size is a big one (forgive the pun <grin>). 

So I’m prone to comparing, and putting into context.

Benchmarks are key here.  Domestic healthcare spend was $2.3 trillion in 2007.  The media/comm market is about $1 trillion (40% of healthcare).  A subset, the domestic advertising market, is approximately $300 billion.  So is Wal*Mart’s annual revenue.  (Actually, Wal*Mart did about $350 billion in 2007.)  Global consumer electronics sales is on the order of $150 billion.  US consulting firms generate about $125 billion annually.  Microsoft is at about a $60 billion revenue run rate.  Domestic pet services is in the $20-25 billion range.  Google did $16 billion in sales last year.  And porn is probably a sub $10 billion market.

And so on and so forth, down the market size ladder.  Plenty of venture investments are made into companies that have potential markets of $1 billion or so.  An example of something this size is the iPhone app market which is projected to be just over a billion dollar market next year.  Smaller firms will have lower thresholds and larger firms, higher ones.

Occasionally, I’ll run into a comparison that surprises or awes.  Wal*Mart has been a long-standing example.  It offers a slew, of course, many related to market share or comparisons to other countries’ GDPs (e.g., about a third of all dog food sold in the US circa 2003 - when I was writing my thesis - was sold at Wal*Mart). 

Last week I struck another:  Lipitor (Pfizer’s cholesterol lowering drug) sales ran on par with or ahead of the internet advertising industry market from 2002-2005 [see relevant charts here and here].

Now, if you know the internet ad space (or at least recall the internet bubble collapse), it’s not a huge surprise that the industry was facing hard times.

It’s remarkable, though, to think that a single drug could reach such heights ($7 - 12 billion), and a continual frustration of new media enthusiasts (the business practitioners, at least) that the online advertising industry didn’t, and still hasn’t, developed more quickly (e.g., 7.5% of advertising was online in ‘07 in the context of 20% of all media being consumed online [Yankee Group stats]).  The growth looks good, though.  Yankee Group projects a $50 billion industry in 2011 (more than double 2007’s figure) and 15% share of the ad dollars.  And Lipitor, well, by then it’ll be facing the drowning water of generics.  Amazing how markets ebb and flow.

Any other comparisons lurking in readers’ heads?  I’d love to see a more comprehensive list of market sizes and/or a graphic that overlays market sizes and company revenues in the $1 - $100 billion range.


Photo credit: Lipitor Does More, originally uploaded by colros

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Accepting of the "New New Thing"? Not Just Yet.

June 19th, 2008

imageControversy walks hand-in-hand with innovation.

It seems, after all, that conversation focused on what’s to be raises hairs. Never mind that we can’t agree on the forecasting. It’s that even when we agree, the outlook may be distasteful.

Consider for a moment John Tierney’s recent piece correlating business lunch deal success with serotonin boosts. Here’s the summary slice:

In an experiment reported in Science, researchers at the University of Cambridge and U.C.L.A. manipulated the diet of subjects and found that people with low levels of serotonin become less likely to make a deal when playing the “Ultimatum Game.”

Don’t worry about what the “Ultimatum Game” is. The punch-line here suggests that food choices might impact a business transaction, or really any interaction focused on parity.

Extrapolating, one reaches an argument I’ve made in the past – that the current hornets’ nest around sports steroids is an early act in what will be an evolving hormone play. The future holds, I believe, cocktail dosing for bursts of charm, salesmanship, endurance, and the like. Or maybe not just bursts, but continuous behavioral alteration.

So here’s where most folks say, “Ugh.” A frightful prospect, “horrid,” (a progressive friend said), unnatural, etc. And rightfully so, perhaps. Perhaps.

One hears similar responses, by the way, to the idea of robot/human love. Or even to the notion of personal information trending public (or concentrating in certain business’ arms), which we’re seeing happen today.

And yet, as my progressive friend smartly points out, it seems that this last trend raises eyebrows and conversational distaste but slowly gains acceptance, a kind of wearing away of the initial disgust.

If we take our innovation in small steps, does controversy melt away? What, then, is the implication of accelerating innovation?

P.S., the following foods are most effective at boosting serotonin levels: “turkey, chicken, fish, pheasant, partridge, cottage cheese, bananas, eggs, nuts, wheat germ, avocados, milk, cheese and the legumes (beans, peas, pulses, soya)” [via]. Not your standard business lunch, btw.


Photo credit: overflow, originally uploaded by *MarS

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Spawning Business

June 15th, 2008

There’s something appealing about viewing entrepreneurship through the lens of evolutionary biology.  Any fruitful niche finds occupants, symbiosis can offer a leg up, and “survival of the fittest” ultimately reigns.  I’m reminded of this November 2006 video from Brad Feld encouraging entrepreneurs to “munch on the bones” of competition (Grendel worthy, by the way):

So extinction is part of the process.  And a rejuvenating element.

Ambling through the halls of the natural history museum in Paris, Olivia Judson weaves the story of death and rebirth in her stellar “Wild Side” NYTimes blog.  She writes:

…each mass extinction has been followed by a pulse of fresh evolutionary change: large numbers of new forms appear. The reason is that before the mass extinction, most niches are occupied — a situation that typically prevents radical changes. Afterwards, many niches are empty and available for re-occupation — which promotes rapid change. (This is why new islands and lakes are always sites of rapid evolution and invention: the few animals and plants that arrive rapidly evolve to fill the various empty niches. Think of the Hawaiian islands, the Galapagos, New Zealand or Madagascar, each of which has — or had, until we got there — a variety of unique animals and plants.)

It’s a pleasure to watch new islands form and spawn endemic businesses in the startup world.  Consider the Facebook application gold rush of a year ago, or the iPhone development craze we’re seeing now, or what will inevitably be an open mobile platform with massive reach and opportunity (3.3 billion mobile phone subs in Nov 2007).

What of this week’s news regarding search advertising consolidation?  Yahoo!’s new partnership with Google (which puts Google ads into Yahoo!’s search results) expands the reach of a nimble elephant and, I suspect, continues to raise the hurdle for competition in the near-term.  Arrington practically calls it a prelude to extinctionWilson claims symbiosis offers a leg up.

Regardless, the market will demand options and I’m encouraged by the thought of thousands of entrepreneurs sitting in crow’s nests yelling, “Land ho!” at the prospect.  Old models die and new ones replace.


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Between Warring Ad Trends, Targeting Prevails

March 25th, 2008

duly ignoredI’ve been thinking about two competing online ad trends:

1) Advertisers/publishers are getting better and better at targeting ads.

2) Consumers are getting better and better at ignoring ads.

Targeting improvements have come on multiple fronts.  Advertisers have an increasing understanding of who is consuming content, in what context, and what exactly is being consumed.  The behavioral ad engines (Tacoda, Aggregate Knowledge, Wunderloop, amongst others) are amassing massive datasets on user behavior to figure out consumer preferences.  Meanwhile, Facebook and other social networks literally hold such information under their nose, embedded in the profile of each of their members.  Content itself is better understood.  Think about the metadata around images or video.  Titles, tags, and comments largely drive ad targeting for these media today, but companies like Digitalsmiths (full disclosure: a Chrysalis portfolio company) are figuring out how to generate improved metadata for advertisers.

At the same time, though, consumers are tuning out.  Tivo/DVR usage is the obvious example, but there are plenty of others.  One can download browser extensions that block advertising while you surf the web.  Eyetracking research indicates that folks ignore banner advertising anyway.  And Starcom, Tacoda, and comScore say that 50% of display ad clicks come from only 6% of the Internet’s users,  folks that aren’t “representative of the general public” and don’t seem to be a particularly lucrative set.

This “sky is falling” backdrop abuts a pretty exciting long-term macro view, though.  Content consumption share continues to shift online (increasing as % of total consumption by medium) and there’s a massive discrepancy between that share and the medium’s share of ad dollars.  Presuming that online engagement can be monetized effectively through advertising, there’s lots of growth potential.  And sure, things could slow down in the short-term as a result of the economic environment, but again, a long-term look at ad spend equilibrium lends a bullish view. 

One would think that as advertisers and publishers get better and better at targeting a point is reached at which consumers stop ignoring.  I’d guess that this outcome requires a more integrated understanding of the consumer.  It requires not just gathering preferences but improved predictive analysis of upcoming consumption decisions.  Let’s call it “implicit search advertising.”  Traditional search advertising works because it catches the consumer with relevant information at the point of a consumption decision.  Surely advertisers will get better at doing this without needing an explicit search (i.e. entering a search into Google).  That future’s coming, and the privacy hounds will be barking at its heels.  Hopefully, “hyper-targeted” meets “opt-in” somewhere along the way.


Photo credit: duly ignored, originally uploaded by niznoz

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Two Types of Entrepreneur: "Alpha" and "Beta"

March 23rd, 2008

image A friend introduced me to a noteworthy line of thinking recently.  It went something like this: “There are two types of entrepreneurs in this world: alpha entrepreneurs and beta entrepreneurs.  Alpha entrepreneurs are the guys that are naturally risk tolerant, even irrational dreamers; they’re charismatic and marshal folks around them to develop a company that’s viable. Alphas take the first step.  Beta entrepreneurs, on the other hand, are very execution focused, basically rational when it comes to risk, and bring to bear a learned skill set. They take problems and set about methodically solving them.  Betas make entrepreneurship work.”

So, my friend says, “We need to stop encouraging alpha entrepreneurship.  You can’t teach someone to be an alpha.  What we can do is teach folks to be betas.  A community doesn’t need a ton of alphas, but it needs lots of betas.”

For me, this classification and accompanying recommendation resonate in certain ways.  Execution builds businesses.  And loads of multi-million dollar businesses are built without a real visionary or need only a creative kick-start.

I do have a couple counterpoints, though: (1) lots of individuals have had their natural alpha suppressed by risk-averse upbringings and a little encouragement can go a long way; (2) a startup’s potential may turn on creative, risky adaptation (in other words it’s not just about a visionary getting the ball rolling; consider Facebook’s application API ingenuity).

Incidentally, the market tends to place a higher value on end-user execution than ingenuity.  Consider invention licensing contracts (pretty favorable to the licensee) or content creation vs aggregation/distribution value allocations (pretty favorable to the aggregator/distributor).  These examples are driven by monetization control but the point holds, I think.

I suspect that my friend has a strong argument from an economic development standpoint.  To “teach betas,” I’d add, “attract alphas.”  Creative juice and leaps of faith are integral aspects of the game, and I’d hate to lose sight of that.  Irrational risk compasses are a precious commodity.


Photo credit: Pink Neon sign, originally uploaded by Browserd

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Imprinting a Legacy

March 15th, 2008

This whole Spitzer hullabaloo has me thinking about legacy.  The New York Times put up an interactive timeline, “Milestones in an Ambitious Career,” that curtly sums the New York Governor’s key career moments into a few pictures and captions.  Here’s the headlining snippet:

“Eliot Spitzer’s journey from Harvard Law School to the highest office in New York state was marked by drive, ambition and [sic] string of successful prosecutions as the state’s attorney general.  But as governor, he stumbled repeatedly and faced humiliation after being linked to a prostitution ring.”

Full stop.  I sure hope Governor Spitzer gets a shot at a third sentence to his legacy.

It’s worth thinking about how one gets described and how we describe ourselves.  The venture industry is pretty unique in that almost every investment professional’s bio is online and readily available.  Ultimately, of course, these are sales pitches (primarily to entrepreneurs).  But some of them hint at or even nail down a legacy; consider John Doerr’s inclusion that his and his partners’ investments have created 150,000 new jobs(!).

What role does the self-described legacy, though, have on the impression of others?  Well, perhaps it’s a guideline (and sometimes a revelation of where one stands on the ego continuum).  Doerr frames himself as a champion of economic development rather than an all-star VC.

The venture industry teaches us to distill a company’s offering into one or two sentences.  How many more does an individual get?  Amazingly, even as our lives become more and more “discoverable” with traces of us digitally archived all over, one’s legacy is, with rare exception, going to be a couple simple sound bites.  One might say, “Tread carefully.”  But I guess I’m more a fan of “give it your damndest and stick to your values.”  What will your two (or three) sentences be?  Worth pondering…