E676: Chris Sacca Matt Mazzeo PT1: Building co's, investing rules, Twitter spills, solutions, buyers

23 Sept 2016 · 59 min
58:48

In this episode of This Week in Startups, host Jason Calacanis sits down with Chris Sacca and his Lowercase Capital partner Matt Mazzeo. The conversation weaves through a wide range of topics: the contrasting roles of Sacca (storytelling, PR, deal sourcing) and Mazzeo (hands‑on operational work), the early‑stage investing philosophy of Lowercase Capital—including a rule to back founders with real‑world experience, a focus on family‑friendly companies, and a willingness to write small pre‑seed checks (as low as $150K). They discuss landmark investments (Twitter, Uber, Instagram, Twilio, Docker, Optimizely) and the personal impact those deals had on their lives. The duo explains how they add value beyond capital, emphasizing narrative crafting, hiring assistance, and press strategy, especially for technically brilliant founders who lack storytelling chops. They dive into niche bets in the esports ecosystem (Smash.gg, MobCrush) and the challenges of evaluating products they don’t personally use. A large portion of the episode is devoted to a deep critique of Twitter’s product and growth problems, potential acquisition scenarios (Google, Facebook, Microsoft, private equity), and the importance of fresh user perspectives. They also touch on Lowercase’s internal product, Lowercase Alpha, and the broader evolution of startup storytelling from the early Web‑1 era to today’s media‑driven expectations. Mid‑episode, the hosts break for a sponsor read promoting IBM’s Smart Camp startup competition, outlining the program’s global reach, mentorship, and prize structure. The conversation also includes lighthearted banter about politics podcasts, a whimsical “Wheel of Bullshit” idea, and a teaser about Mazzeo’s involvement in an esports team house, reinforcing the playful dynamic between the hosts. Throughout, the core dialogue reveals the partners’ investment criteria, operational philosophy, and views on the future of key portfolio companies, while sponsor reads and casual jokes provide contextual flavor.

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