This Week in Venture Capital

I recently interviewed Matt Mazzeo of Lowercase Capital. By now most of you know that Chris Sacca invested in what is now thought to be one of the best performing VC funds of all time having invested an $8.4 million fund in: Uber, Instagram, Docker and Twitter, amongst others. He then went on to build perhaps the largest single shareholding in Twitter. But did you ever wonder how Matt Mazzeo, who’s in his early 30s became Chris’s partner?

In many ways I wanted to focus on Matt because to those of us in the LA Venture community Matt really has become the public face of Lowercase Capital over the past several years. He has won many over (including me) through his hustle, his relationship, his service approach to venture and the fact that he is, frankly, a very likable and humble guy.

The viewer above (big thank you to ClipMine) will allow you to skip forward to key moments by clicking on the contents tab on the left but to give you some insights on Matt.

Matt joined Lowercase by working the scene at SXSW on behalf of CAA where he worked in business development. If you don’t know CAA it’s one of the two most prestigious talent agencies in Los Angeles representing writers, directors, actors, musicians and so forth. He spent the evenings having tech debates with the likes of Gary Vaynerchuk, Travis Kalanick, Garrett Camp and … Chris Sacca. I wrote about my own experiences with these late-night debates four years ago: The Magic Midnight Mind Meld.

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Product Hunt. It seems out of nowhere it has become the go to website for startup companies to launch their new products or businesses.

It reminds me a lot of how TechCrunch felt in 2006. It was the place that every startup knew they HAD TO be in order to attract initial users and also gain the attention of venture capitalists. A strong showing on TechCrunch created initial product demand and if you could sustain that it led to buzz overall in the tech community. Companies like Twitter were really cultivated by the TechCrunch enthusiast crowd long before celebs, comedians and politicians were on Twitter.

And if you need the parallel look no further than Meerkat whose success was highly correlated with its popularity in the Product Hunt community and it leveraged the tech industry buzz around the product into more meaningful usage by people like Jimmy Fallon or U2.

So I set out to understand this phenomenon a bit more deeply. I started by launching a portfolio company’s product on Product Hunt.

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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

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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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