Both Sides of the Table

I become a venture capitalist in September 2007 – exactly 6.5 years ago.

I spent my first year developing proprietary deal flow and learning the business and then the Sept 2008 / Lehman Bros collapse / financial meltdown happened.

As a result I didn’t write my first venture capital check until March 2009 – exactly 5 years ago. That company was Invoca, which just announced a $20 million fund raise led by Accel.

I remain a huge supporter and am very proud of our accomplishments and hugely optimistic about our future.

5 years ago. It turns out it actually takes time to build a high-growth business with differentiated intellectual property and roll out large, enterprise-class marketing solutions. I remember a few years ago people (LPs mostly) used to ask me why I didn’t have any realized returns to show. At the time I pointed out:

“If I had realized exits almost certainly it would be because I invested in a company that failed. Lemons ripen early, great companies take time.”

Still. It was frustrating having to answer what I considered an obvious question to people who I thought would have known better.

In 2010 somebody posed the question on Quora, “Is Mark Suster a Successful Venture Capitalist?” I thought it was a fair question and I gave an honest answer at the time.

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We all intuitively know how important human connections are in business but for many people it’s like exercise or eating well – one of those things you keep meaning to get around to.

It reminds me of a line my wife and I often jokingly say to each other after seeing the awesome film “Notorious” about the life of Biggie Smalls

“I know mothafuckas who know mothafuckas.”

Please just take 8 seconds to listen to this clip on YouTube – it’s priceless. It always struck a chord with me. The critical skill is not just your immediate network but the network beyond that you can tap into if you’ve earned the right through nurturing your 1-degree relationships.


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This article originally appeared on TechCrunch. There is an old saying in poker that if you don’t know who the sucker at the table is – it’s you.

The same can be said of critical decisions in a board meeting or frankly any other meeting where major decisions are ratified. If you’re turning up to important meetings hoping to persuade the critical people who attend of a decision you’re trying to make and having already “counted your votes” you are sub-optimizing results.

This is a classic mistake many entrepreneurs make so I’d like to offer some constructive advice on how the savvy hand would be played.

1. Why You Should Pre-Meet Board Members
It is healthy to allocate 30 minutes per board member for a call at least a week in advance of your board meeting.

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Almost every startup company starts off “scrappy” and there’s a well established culture in the tech startup scene to embrace the “be cheap at all costs” mentality.

So we have the proverbial garage startup or the small team working on desks that are handmade out of scrap wood or former doors from a construction site. But at what point do you need to flip from scrappy to “scale-y”? Um, well, that word choice doesn’t exactly work.

I have seen this problem up close so many times. You have a seed-stage company who had raised $500,000 and then later raises $8 million still acting like a seed-stage startup. Similarly you have the A-round company who has raised a $25 million round still behaving like a 10-person startup with the CEO still micro-managing every decision.

I have weighed in on this topic before. I wrote that the most controversial hire after an A-round is actually an office manager / admin person for the company.  My rationale is simply.

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By now you likely know that Marc Andreessen weighed in on anonymous apps in a 12-part Twitter diatribe.

Anonymity. As the old joke goes, “on the Internet nobody knows you’re a dog.”

I have been weighing in slowly on the topic over the past few weeks on Twitter but have avoided writing a blog post about it until now. This was in part due to a tremendously busy 30-day period for me (in which my overall writing has been down) and in part the inevitability of knowing that weighing in just tees me up to take abuse on one anonymous app called Secret.

I have thought a lot about anonymity over the years and actually have enjoyed debating the topic with those passionate about anonymity’s benefits because of course that’s how I learn.

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