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. Chris & Matt had that mind meld and were very complementary, had an aligned vision and decided to work together.

Matt learned the “client service” approach to venture capital or startups by working at CAA and credits Richard Lovett with having taught Matt the importance of client service. Matt says that this service approach has helped Lowercase really win the loyalty of the founders they back in a market that has grown increasingly competitive.

We spoke at length about seeking out mentors and how to get the most out of them. We recounted my own experiences with Matt where we would go to breakfast and he would ask for feedback by saying, “Go ahead. Beat the shit out of me. What could I be doing better?” And despite the shock of the direct approach you could tell he was sincere.

https://soundcloud.com/bothsidestv/matt-mazzeo

We spoke about how we both like to back entrepreneurs with a healthy chip on their shoulders and a desire to stick ones middle finger up at the establishment. You can often tell how immigrants or people who came from modest means but are driven to succeed are often on a mission do achieve extraordinary results at almost any cost. In fact, Matt personally grew up with hardships but you wouldn’t know it because he gives off such a positive energy you could imagine he lived the life of Riley.

Matt’s father had medical difficulties due to his service in the Vietnam War and as a result for much of Matt’s later childhood he was raised and provided for by his mom, who worked hard to provide for her family. Matt was smart enough to have gotten a full scholarship to one of LA’s top high schools (Harvard Westlake) and later a full ride to Harvard. As a result Matt feels compelled to give back to Harvard Westlake to provide similar opportunities for economically challenged individuals.

We then had a follow-on conversation about race and the many biases that are subconscious about the word choices, accents, intonations and cultural differences that a lower-income black or Latino faces that make life even harder for an economically disadvantaged minority. For all that Matt has overcome (and truly I take my hat off to him), he still looks and sounds and acts like all of the people of white, privileged executive class in US. And we as a society have to do better at providing public schooling and economic opportunities for people of all backgrounds if we’re really going to have a level playing field in this country.

We spoke about all that and if you watch the video you can hear what we had to say.

Thanks for doing the show, Matt. It’s always such a pleasure to spend time with you, learn from your perspectives and debate our topics of the day.

As always, you can subscribe to my YouTube channel, Soundcloud and podcast RSS feed.

And finally for powerusers, you might have noticed I release clips from each interview on Vidme (recently crossed 100k plays!). You can follow me there as well.