Are you practicing too much?

Posted on June 22, 2011 by

Darth Vader practicing in the mirror.Practice makes perfect. Whether memorizing lines for a play, learning to play a rockin’ guitar solo, or pitching your company, practice is an important part of getting your message across. Everyone knows this, so everyone practices as much as they can.

I rarely come across an entrepreneur who hasn’t practiced his pitch to some degree of satisfaction. What I do see, sometimes, is what I believe to be the opposite problem: too much practice.

How can too much practice be detrimental? When it erodes the spontaneity of a performance.
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Posted in Advice, Entrepreneurship | 1 Comment

The puzzle piece that doesn’t exist.

Posted on June 10, 2011 by

The mystery of the Mayan calendar revealed!(Warning: this post gets a bit “meta.”)

After 10 years of iTunes usage, I finally shelled out $17.99 to buy my first audiobook: Malcolm Gladwell’s What the Dog Saw. With Gladwell seemingly whispering in my ear in his unmistakable tenor, the 5-hour Memorial day car trip simply flew by.

The book contains lots of great nuggets, all drawn from Gladwell’s long career writing for The New Yorker. While any of these could inspire a blog post, I was particularly drawn in by “Open Secrets: Enron, intelligence, and the perils of too much information.”

I quote from the full article, which you can find here in its entirety.
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Posted in Advice, Entrepreneurship, Venture capital | 2 Comments

But, does it scale?

Posted on June 1, 2011 by

Venture capitalists can ask a bunch of dumb questions.

Well, maybe “dumb” is the wrong word; “repetitive” is probably more accurate. How many times do you have to explain how you acquire users, how big your market is, or what the competitive response will be to your product? It can get pretty frustrating, especially if you’re actually turning poop into gold.

I think conference panels exacerbate this frustration, especially those “lightning pitches” wherein a number of judges has to instantly critique a business plan they know almost nothing about. I’d estimate that 90% of the questions judges ask on these things are the same 10 questions. And, the one that is always included is:

How do you scale?

This question is almost never answered properly. I think it’s because “scale” is not well-defined in common discourse. Here’s my attempt to put a framework around it.

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Posted in Advice, Entrepreneurship, Software, Technology | 4 Comments

interview to venture: Episode 1, CampusLIVE

Posted on May 18, 2011 by

This week, I took a break from the written word and videotaped myself interviewing Boris Revsin, CEO and co-founder of one of Highland’s newest portfolio companies: CampusLIVE.

I’ll be doing more of this in coming weeks, so stay tuned for more clips from the interview to venture series. I hope you enjoy a brief glimpse inside the mind of one of the entrepreneurs we have the privilege of working with.

Posted in Advice, Entrepreneurship, Interview | 1 Comment

VCs buy your stock, not your product.

Posted on May 12, 2011 by

Door to door sales cat.Last Friday, I had the honor of speaking on a panel at the MIT Sloan Sales Conference, alongside Peter Levine (MIT, Andressen Horowitz), George Roberts (ex-Oracle, OpenView Partners), Jules Pieri (The Daily Grommet), and Lara Shackelford (QlikTech). No one has ever taught me sales formally, but I find it fascinating and have the privilege of working with several ex-sales guys at Highland. I also find myself on the receiving end of multiple pitches each day, so I have begun to envision raising money as a sales process itself.

There are many similarities between selling product and raising money. Both require progression through a sales funnel, which starts with lead generation and ends with a close. Also, both require aggressive time management and the constant re-allocation of resources towards the most promising leads. Finally, both suffer from a classic adverse selection bias, wherein what is easy is not what is desirable. Put differently, VCs often want what they can’t have. Managing their level of interest lies at the heart of the sales process.

The metaphor, however, is not perfect. Selling a customer and selling a VC differ greatly in one respect:

Customers buy product. VCs buy stock.

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Posted in Advice, Entrepreneurship, Product philosophy, Venture capital | Leave a comment

3 traits of compelling internet products

Posted on May 3, 2011 by

While the world was celebrating the death of Osama bin Laden yesterday, my first post went up on Mashable. In it, I talk about the 3 qualities I look for in compelling consumer internet products: ego, serendipity, and familiarity.

You can find the post here. Please check it out and leave me a comment if you like it!

Posted in Entrepreneurship, Product philosophy | Leave a comment

Interviewing the Yoda of venture capital

Posted on April 28, 2011 by

The yoda of venture capital.I’ve been a bit absent from this blog, thankfully working on some very exciting projects that will soon see the light of day. More blogging to come soon, so hang in there!

In the meantime, I would like to draw your attention to an excellent interview by Jim Connolly of Mass High Tech of Paul Maeder, co-founder of Highland Capital Partners (and my boss). Paul has been in the venture business for about 30 years and has backed game-changers like Avid, Checkfree, Sybase, Vertica, Vistaprint, and many others. He is also Chairman of the National Venture Capital Association (NVCA) and is fighting the good fight in DC on behalf of our entire industry.

Friend and fellow VC at Village Ventures Matt Harris has also called Paul “the Yoda of venture capital.” Better grammar though.

Jim was nice enough to allow me to reblog parts of the interview below. If you want to see Jim’s entire interview, go here.
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Posted in Advice, Venture capital | 1 Comment