Both Sides of the Table


Venture Capital is a tricky industry. If you’re funding the same stuff as everybody else and if you started your activities when the clues were obvious you’re much less likely to drive enormous returns.

When Fred Wilson funded Twitter I guarantee you it wasn’t obvious that it was a billion dollar+++ idea. Far from it. Many questioned whether it could survive under the fail whale, inevitable competition from Facebook, founder fighting, fights with 3rd-party developers let alone become a revolutionary business that could make money. Lots of it. He couldn’t have imagined power users would be global political figures, dictatorships, small factions of people standing up to the Iranian army or every sports figure & celebrity in the world.

It was an early and smart bet.

When the early teams: angels, lowercase capital & first round capital funded Uber they had no idea it would be one of the most revolutionary ideas of our time. I know – I was there when the first people debating funding it at less than a $5m valuation.

Airbnb? Ha. Almost nobody believed and now look at it.

Drones. Bitcoin. Online education. VR. Palantir. There were many moments in each space when pioneers were funding startups and the press hadn’t written much about them and if you were a typical investor you were still funding the last trend while some VCs were trailblazing into new categories.

As is often said if you don’t get at least a few fellow VCs (and entrepreneurs) scratching their heads you may not be funding ideas with enough upside. This was certainly the case when I invested in a small YouTube video production company called Maker Studios that recently sold to Disney for just shy of $1 billion.

Internally at Upfront Ventures we talk about “high consensus” vs. controversial deals with “high conviction.

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I wrote a version of this post four years ago but given the hectic nature of today’s tech markets I thought it was worth revisiting and updating.

Canceling meetings is a part of modern day life.  I seem to get so over programmed that if I ever want to have a “break-out” unplanned trip somewhere I seem to have to reschedule meetings. Not fun, but a reality.

People reschedule meetings with me on a regular basis, too.  If done correctly I never have any problem with it at all.

When you do need to reschedule a meeting make sure to put yourself in the other person’s shoes.  Give reflection to what inconvenience you may be causing.  Make sure you’re mentally aware of whether they might have made special plans around your meeting.  Basically, don’t be cavalier about rescheduling meetings.

Let me give you an example.  A couple of years ago an entrepreneur had requested a meeting with me to present his business.  A friend that I respect had introduced me and asked me to meet with the guy.  I always try my best to take meetings like this since my friend had clearly committed some political capital to his friend in saying he could help him get a meeting.

The meeting was set for Wednesday, May 8th at 11am.

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Everybody has a blog these days and there is much advice to be had. Many startups now go through accelerators and have mentors passing through each day with advice – usually it’s conflicting. WTF? There are bootcamps, startup classes, video interviews – the sources are now endless. What is a founder to do?

There are some smart if not somewhat cerebral bloggers I read who say that you shouldn’t take any startup advice at all because it’s too generalized to be useful to your situation. While I have some sympathy with their intent I must point out that their opinions on this are – ironically – startup advice. And not a point-of-view I particularly believe in.

So what IS one to do?

1. Triangulate
I like to use the shorthand “triangulate” to symbolize asking multiple people for their opinions to get a better perspective on the route you should take. Of course triangulation is a mathematics term that is used in sailing and other activities to help you better navigate when you don’t have your bearings. By having the measurement of some known points you can better navigate to unknown points through inference.

I triangulate in nearly every important decision I make.

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Just back from vacation and also some work travel and want to get back to blogging so expect a few posts over the next couple weeks.

During my absence I posted a couple new episodes of Bothsides TV recently. I’ll try to get write-ups shortly but for now here is an overview of my interview with Nanea Reeves – President and COO of textPlus. I could have listened to her for hours as many of her lessons were ones I hadn’t heard before such as how she used online gaming when she was younger as a way of both teaching herself tech as well as learning to lead remote teams.

Just so you know I work directly with Nanea and her arrival last year at TextPlus as President & COO has been transformational for the company. I’m sure I would speak for the entire board and management team in asserting this. I’ll try to do a future blog post on some of my insights in watching Nanea enter the role and how the founders enabled her success.

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Last Wednesday I had coffee with an old friend and former colleague. We haven’t worked together in a while and were reminiscing about the old days. I miss the old days when we used to be locked in battle together on the issues affecting our company.

Seeing him again also reminded me of one of my first big lessons as a VC – knowing when giving in is more important than being right. So I Tweeted that the next morning:

“When the consequences of “being right” are not great enough sometimes graciousness & conceding is a better option”

Yes. Of course it’s a universal lesson and one that I’m doomed to learn over and over.

I wrote about it in this widely read post, “Be Gracious When it’s Time to Give In.

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