Founders: Are you Leaning far Enough?

Posted on November 10, 2010. Filed under: startups, venture capital | Tags: , |

I don’t write very much about my relationship with my partner Kenny Lerer, mostly because he’s not really one for the spotlight, but lately I’ve been thinking a lot about the things I’ve absorbed from him over the past 10 months or so.  Yesterday at a breakfast I caught myself advising a young Dartmouth graduate with words that were not in my vocabulary before Kenny became my partner at Lerer Ventures and Hyperpublic.

This particular breakfast, I found myself listening to a relatively analytical young guy who had obviously spent a lot of time thinking about his next moves.  For some reason there was friction between his decions and subsequent actions.  What I told him, which is advice that Kenny has given me and other founders I know repeatedly, is that he really needs to “lean into” the direction that he’s decided to go in.

It sounds like a minor point, but I believe that this mentality is the difference between grounding out to the short stop and hitting a line drive into left field.  Many good entrepreneurs and strategists are able to assess a situation and make a good decision (let’s call that “pitch selection”), but that is only part of what makes you a great batter.  I’ve always been good at deciding what pitch to swing it, but there’s another decision after “pitch selection” that is extremely important.  Let’s call that decision “commitment to the pitch.”  If you decide to swing but sit on your heels and slap at it, you’ll poke the ball through sometimes, ground out frequently, but often make contact.  I’ll call that low commitment, low risk.

On the other hand, if you “lean into” the pitch, get on the balls of your feet, and swing hard and all the way through the ball without hesitation, your contact and results will be much stronger when you connect.  Granted, you’re going to whiff more often, and that curve ball is going to leave you on your ass in the batters box, but generally speaking, I believe you’ve got a better chance of putting the ball where you want to with this approach.

What I’m seeing is that despite much nuance in the course that you charter for a go forward strategy, exaggerating the most important aspect of your ultimate destination sets a tone and point to drive to that may be a simplification of the vision, but a necessary means to landing where you want to land.

So Kenny would say, and I think I agree, if the most important thing at Hyperpublic is that we end up achieving hyperlocality, despite an incredibly complex path to get there, we as a company really need to “lean into” that aspect of our product and our future.

Isolate the goal, exaggerate it, and don’t be afraid to commit heavily to what you’ve decided is correct.  Are you leaning far enough?

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The Blurring Line between Commerce and Ad Models

Posted on March 11, 2010. Filed under: startups, venture capital | Tags: , , , |

A lot of different ideas are converging in my head right now, largely as the result of two discrete conversations.  The first, is more of a broad thesis I am developing about alternative revenue streams for publishers, and how niche publications are thinking about monetizing their audience and assets beyond “ad models.”  The second is a thesis I’ve been kicking around in the realm of Charlie O’Donnels NextNY conversation last night on “Disruptive Commerce Models” or “E-Commerce 2.0.”

Until last night, I largely viewed realms to be separate, but a conversation this morning with a very bright guy named David Cho made me realize that one of the fundamental drivers influencing my thinking in both realms is related  to a broader phenomenon:

Phenomenon: The line between commerce and advertising is blurring.  Think of the relationship between the below monetization mechanisms as a spectrum, where both ends of the spectrum are losing $ volume to the middle:

The Commerce/Ad Spectrum

Commerce 1.0 (buying inventory, taking risk, reselling at a premium to consumer)

“Commerce light” (no inventory, really brokerage between suppliers and consumers)

CPA (performance)

CPC (performance)

Brand Advertising

I see tons and tons of niche publishers looking to “transform” their model away from “ad models” toward “commerce models” (largely chasing what they perceive to be the strategy that made Gilt grow like a weed).  David Cho was the first niche publisher I have met since I started investing who said “fuck that, the ad-model isn’t broken, I just need better units to monetize my base.”  I actually think he may be right…but those better performing units are going to start to look more and more like commerce functions. is a perfect example of an ad based model that really operates and feels like a transaction/commerce model to consumers…now, think about a world where widgets being distributed onto publishers sites, are capable of performing transactions and transaction like events within the ad unit…and you start to see where I’m going with this.  So that’s advertising bleeding up the spectrum into commerce…

Now let’s look at commerce bleeding down spectrum to advertising.  Last night’s conversation at NextNY was theoretically about Commerce startups, but in reality, I didn’t know how to define “Commerce” or an “e-retailer” any more…the reason is because so many of the folks in the room pursuing flash sales, group buying, etc…aren’t really retailers at all.  They are more like brokers, bringing together suppliers and consumers.  Is a broker a retailer?  Because these brokers are similar to retailers, but brokers also look an awful lot like ad units…bringing together suppliers and consumers for a fee (without taking inventory risk).

All of this is to say I don’t think there is a hell of a lot of difference between Ad models and “commerce light” models when applied to an audience aggregated through some sort of editorial voice…so I’m interested in talking with people who are pursuing the nexus point of these two worlds, especially if you are packaging that together into a “turnkey” monetization mechanism and selling into publishers.  If you are…and you’re smart…I’m interested in learning from you and maybe even investing in you.

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    I’m a NYC based investor and entrepreneur. I've started a few companies and a venture capital firm. You can email me at (p.s. i don’t use spell check…deal with it)


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