This Week in Venture Capital

If you are a 20-something tech entrepreneur you could be forgiven for thinking that seed-stage investors, Angellist Syndicates and widely available angel money always existed. It is, of course, a very recent phenomenon.

Let me take you back just 10 years ago to 2005 in Silicon Valley where I returned after 11 years of living in Europe. I was out to raise my first seed money in my second startup of $500,000. I began asking around who the likely investors were for such a market. At the time almost nobody had heard of the following funds: FirstRound Capital, TrueVentures, Floodgate and SoftTech. I think they were all brand new or just forming.

Firms like Baseline, Felicis, ff Ventures, Founder Collective, Freestyle, HomeBrew, IA Ventures, K9, Lowercase, NextView, Resolute, Rincon, Crosscut and the countless other great firms we all now know didn’t exist. Neither did Y Combinator, 500 Startups, TechStars, Amplify, Mucker and countless others.

There was Ron Conway (SV Angel) – I think there was always Ron Conway! one of the godfather’s of our industry. And some angels running around like Reid Hoffman & Keith Rabois. But not many others.

If you want to understand the software trend that drove the creation of the seed-stage VC phenomenon I wrote about it that linked blog post but in short: cloud computing drove down the cost to create startups enabling a new category of investor.

But back in 2005 there were a few people who spotted the trend before others and one of the true pioneers was (and continues to be) Jeff Clavier who founded SoftTech VC.

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My blog had been looking tired for a year or two. The problem is that with WordPress I just found it a bit too cumbersome to change the design on my own.

I’m more of a verbal content guy. I like to get what is in my brain out into words and as you probably know I worry less about typos, grammar or – generally – visual design. I appreciate beautiful design – I just wasn’t blessed with the skill of producing it.

I considered changing to a blog publishing platform that would allow me to change the visual design more easily myself. But that seemed too much work for me.  And I tried a couple of times unsuccessfully to pay designers to do sketches for me of how it could look. But when you’re not a designer it’s hard to translate your sense of aesthetic to somebody else.

And then Jess Bachman came to my rescue.

We had collaborated before. Jess reached out to me a few years ago and suggested we team up on An Infographic about Dilution in Startups.

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It all started in 2010 with Klout. I wasn’t a believer. I had always liked and respected CEO Joe Fernandez but could never get my head around the fact that the Klout was putting up charts showing who influenced me and it didn’t map to the reality I knew in my head.

I had been trading emails & Tweets with venture capitalist John Frankel and we were to meet in person in March 2011 at SxSW to talk about Klout and other investments he had made. We met at a private party hosted by his venture partner Mike Yavonditte and I outlined my concerns for the lack of precision of the algorithm.

I was used to this debate. I had been hanging around Klout for a year and many of my friends had angel funded the company and were champions. Nobody had any sound logic on why Klout would be successful.

John laid into a well-honed thesis on why the social web needed a “Page Rank” equivalent for people. He was an early investor in Klout and was the most compelling voice I had heard on why the company would become hugely relevant.

Other people were convinced including Kleiner Perkins

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Tracy DiNunzio isn’t your typical Silicon Valley startup founder. She’s a painter and a self-proclaimed Bohemian. She did her first tech startup after the age of 30. And she didn’t start her company in Northern California.

Tracy built her company, Recycled Media, out of necessity. She hasn’t raised any venture capital. She drove her company to profitability before paying herself a modest salary.

She leveraged herself and even sold many of her possessions to get started. And when her assets were tapped she rented out her bedroom and even her couch on Airbnb to afford her year-one operations. More on that later.

She actually IS the prototypical entrepreneur. Just not the kind you would initially read about on TechCrunch. That may soon change. And that’s what I love about her narrative.

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There are very few people in Silicon Valley who have such a precise grasp on what defines success of early-stage startup companies than Eric Ries. And there are very few people who so consistently exceed my expectations when I hear them speak. I find myself nodding – even when the topic is one I don’t expect to agree with such as “fail fast.”

This week was no exception. I interviewed Eric for an hour for – This Week in Venture Capital. What’s awesome is that the ThisWeekIn team now does time coding so you can go directly to the section in the video you want to hear (you need to click on link for video and then below the video in YouTube the links to the exact times will take you to that section in the video).

We had a wide-ranging discussion which included discussions of Eric’s early career (including his failures), how he came to focus on the Lean Startup movement (at the encouragement of Steve Blank who was an investor in the company he co-founded) and what he wants to do next.

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I’ve often wanted to let people see what a VC pitch is like to help new entrepreneurs have a better sense of what it’s like to present.

Obviously having a camera on will add a small bit of an artificial result because I don’t want to ask as much confidential information and with the camera on people are obviously a bit nicer.

But this interview is fairly authentic. If you like it I’ll do more and continue to strive for authenticity.

So here are Sahney Nager & Ryan Weber of Smarketplaces. I really like them. But I also asked some tough stuff. The video link is here.

Hope you enjoy.

Feel free to provide any feedback on the format or how to make it more authentic. And wether seeing pitches of useful to you or not.

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